CN1551885A - 环状吲哚和杂吲哚衍生物、其作为药物的制备和用途 - Google Patents
环状吲哚和杂吲哚衍生物、其作为药物的制备和用途 Download PDFInfo
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- CN1551885A CN1551885A CNA028172639A CN02817263A CN1551885A CN 1551885 A CN1551885 A CN 1551885A CN A028172639 A CNA028172639 A CN A028172639A CN 02817263 A CN02817263 A CN 02817263A CN 1551885 A CN1551885 A CN 1551885A
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- alkyl
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- AMQFJJCJOSCKNY-UHFFFAOYSA-N methyl hydrogen sulfate;pyrazine Chemical compound COS(O)(=O)=O.C1=CN=CC=N1 AMQFJJCJOSCKNY-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000002438 mitochondrial effect Effects 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
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- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed systems
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- C07D515/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D515/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D515/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D515/14—Ortho-condensed systems
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Abstract
本发明涉及通式(I)的新颖的取代的、增环的吲哚和杂吲哚衍生物其互变异构体、立体异构体、混合物和药学上可接受的盐,还涉及其作为药物的制备和用途,特别作为抗肿瘤剂,用于哺乳动物,特别是人类。
Description
本发明涉及式I的新颖的取代的吲哚和杂吲哚衍生物
其互变异构体、其立体异构体、其混合物和其药学上可接受的盐,还涉及其作为药物的制备和用途,特别作为抗肿瘤剂,用于哺乳动物,特别是人类。
2000年4月28日的德国专利申请(Patent ASTA Medica AG withPrivatdozent Dr.Mahboobi)描述了经由对应的2-锂吲哚制备2-酰基吲哚的方法。
Theophil Eicher and Ralph Rohde,Synthesis 1985,pp.619-625描述了1,2-二苯基-3a-氮杂环戊二烯并[a]茚-3-酮的制备。既没有公开也没有提示所述化合物的医药应用。
按照本发明的一个方面,提供了式I化合物,或其互变异构体、立体异构体、混合物或药学上可接受的盐:
其中
R1是氢、(C6-C14)-芳基——它是未取代的或者被相同或不同的取代基完全或部分取代、(C1-C13)-杂芳基——它含有至少一个至四个N、NH、O和/或S作为环成员并且是未取代的或者被相同或不同的取代基完全或部分取代、(C3-C8)-环烷基——它是未取代的或者被相同或不同的取代基完全或部分取代、或者直链或支链(C1-C20)-烷基——它是未取代的或者被相同或不同的取代基完全或部分取代;
A、B、C或D彼此独立为被R2-R5取代的氮原子或碳原子;
R2、R3、R4和R5彼此独立为游离电子对(如果键合伴侣A、B、C或D是氮原子)、氢、卤素、氰基、硝基、羟基、直链或支链(C1-C6)-烷基、被一个或多个卤原子取代的直链或支链(C1-C6)-烷基、直链或支链(C1-C6)-烷氧基、被一个或多个卤原子取代的直链或支链(C1-C6)-烷氧基、直链或支链(C1-C6)-亚烷二氧基、(C1-C6)-烷基羰基氧基、(C1-C6)-烷氧基羰基氧基、(C1-C6)-烷硫基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、羧基、(C1-C6)-烷基羧酸酯、酰胺、N-(C1-C6)-烷基酰胺、N,N-二-(C1-C6)-烷基酰胺、(C1-C6)-烷氧基-(C1-C6)-烷基、氨基、单-(C1-C6)-烷基氨基、二-(C1-C6)-烷基氨基——其中两个(C1-C6)基团一起可以构成可选含有一个或多个NH、N-(C1-C6)-烷基、O或S的环、(C6-C14)-芳基、(C6-C14)-芳氧基、(C6-C14)-芳基-(C1-C6)-烷基、(C6-C14)-芳基-(C1-C6)-烷氧基-(C1-C6)-烷基、(C1-C6)-烷基羰基、(C1-C6)-烷氧基羰基、羟基,其中两个直接相邻的基团可以彼此连接;
R6是(C6-C14)-芳基——它是未取代的或者被相同或不同的取代基完全或部分取代、(C1-C13)-杂芳基——它含有至少一个至四个N、NH、O和/或S作为环成员并且是未取代的或者被相同或不同的取代基完全或部分取代、(C3-C8)-环烷基——它是未取代的或者被相同或不同的取代基完全或部分取代、直链或支链(C1-C20)-烷基——它是未取代的或者被相同或不同的取代基完全或部分取代,其中相同或不同的取代基选自氢、氟、氯、溴、碘、氰基、硝基、羟基、(C1-C6)-烷基、(C1-C6)-烷氧基、羧基、被一个或多个相同或不同的卤原子取代的(C1-C6)-烷基、被一个或多个相同或不同的卤原子取代的(C1-C6)-烷氧基、直链或支链(C2-C6)-烯基、直链或支链(C2-C6)-炔基、(C3-C8)-环烷基、直链或支链(C1-C6)-烷氧基、直链或支链(C1-C6)-亚烷二氧基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C6-C14)-芳基、(C6-C14)-芳基-(C1-C6)-烷基、(C6-C14)-芳基-(C1-C4)-烷氧基-(C1-C6)-烷基;
X是羰基(C=O)、亚砜(S=O)或磺酰基(SO2);
Y是氧原子或被基团R7取代的氮原子(NR7),其中
R7是(C6-C14)-芳基——它是未取代的或者被相同或不同的取代基完全或部分取代、(C1-C13)-杂芳基——它含有至少一个至四个N、NH、O和/或S作为环成员并且是未取代的或者被相同或不同的取代基完全或部分取代、(C3-C8)-环烷基——它是未取代的或者被相同或不同的取代基完全或部分取代、直链或支链(C1-C20)-烷基——它是未取代的或者被相同或不同的取代基完全或部分取代,其中相同或不同的取代基选自氢、氟、氯、溴、碘、氰基、硝基、羟基、(C1-C6)-烷基、(C1-C6)-烷氧基、羧基、被一个或多个相同或不同的卤原子取代的(C1-C6)-烷基、被一个或多个相同或不同的卤原子取代的(C1-C6)-烷氧基、直链或支链(C2-C6)-烯基、直链或支链(C2-C6)-炔基、(C3-C8)-环烷基、直链或支链(C1-C6)-烷氧基、直链或支链(C1-C6)-亚烷二氧基、(C1-C6)-烷氧基-(C1-C6)-烷基、直链或支链单-(C1-C6)-烷基氨基、直链或支链二-(C1-C6)-烷基氨基——其中两个(C1-C4)基团一起可以构成可选含有一个或多个NH、N-(C1-C6)-烷基、O或S的环、(C6-C14)-芳基、(C6-C14)-芳基-(C1-C6)-烷基、(C6-C14)-芳基-(C1-C4)-烷氧基-(C1-C6)-烷基、(C1-C6)-烷基羰基、(C1-C6)-烷氧基羰基;
n是0或1,其条件是如果n=0,那么
Z是被基团R8取代的碳原子(C-R8),其中
R8是(C6-C14)-芳基——它是未取代的或者被相同或不同的取代基完全或部分取代、(C1-C13)-杂芳基——它含有至少一个至四个N、NH、O和/或S作为环成员并且是未取代的或者被相同或不同的取代基完全或部分取代、(C3-C8)-环烷基——它是未取代的或者被相同或不同的取代基完全或部分取代、直链或支链(C1-C20)-烷基——它是未取代的或者被相同或不同的取代基完全或部分取代,其中相同或不同的取代基选自氢、氟、氯、溴、碘、氰基、硝基、羟基、(C1-C6)-烷基、(C1-C6)-烷氧基、羧基、被一个或多个相同或不同的卤原子取代的(C1-C6)-烷基、被一个或多个相同或不同的卤原子取代的(C1-C6)-烷氧基、直链或支链(C2-C6)-烯基、直链或支链(C2-C6)-炔基、(C3-C8)-环烷基、直链或支链(C1-C6)-烷氧基、直链或支链(C1-C6)-亚烷二氧基、直链或支链(C1-C6)-烷硫基、(C1-C4)-烷基亚磺酰基、(C1-C4)-烷基磺酰基、(C6-C14)-芳硫基、(C6-C14)-芳基亚磺酰基、(C6-C14)-芳基磺酰基、(C1-C6)-烷氧基-(C1-C6)-烷基、直链或支链单-(C1-C6)-烷基氨基、直链或支链二-(C1-C6)-烷基氨基——其中两个(C1-C4)基团一起可以构成可选含有一个或多个NH、N-(C1-C6)-烷基、O或S的环、(C6-C14)-芳基、(C6-C14)-芳氧基、(C6-C14)-芳基-(C1-C6)-烷基、(C6-C14)-芳基-(C1-C4)-烷氧基-(C1-C6)-烷基、(C1-C6)-烷基羰基、(C1-C6)-烷氧基羰基、直链或支链单-N-(C1-C6)-烷基羰基氨基、直链或支链二-N,N-(C1-C6)-烷基羰基氨基、直链或支链单-N-(C1-C6)-烷氧基羰基氨基、直链或支链二-N,N-(C1-C6)-烷氧基羰基氨基、直链或支链N-(C1-C6)-烷基羰基氨基-N-(C1-C6)-烷基氨基、直链或支链N-(C1-C6)-烷氧基羰基氨基-N-(C1-C6)-烷基氨基;
并且如果n=1,那么
Z是氮原子。
按照本发明的进一方面,提供了这样的化合物,其特征在于R1是氢,R2、R3、R4和R5彼此独立为氢、卤素或(C1-C6)-烷氧基,R6是直链或支链(C1-C20)-烷基—它是未取代的或者被相同或不同的取代基完全或部分取代,或者是(C6-C14)-芳基—它是未取代的或者被相同或不同的取代基完全或部分取代,其取代基选自(C1-C6)-烷氧基和卤素,Y是氧原子或基团N-R7,其中R7是(C6-C14)-芳基—它是未取代的或者被相同或不同的取代基完全或部分取代,X是羰基(C=O),Z是氮原子,n=1。
按照本发明的进一方面,提供了这样的化合物,其特征在于R1是氢,R2、R3、R4和R5彼此独立为氢、卤素或(C1-C6)-烷氧基,R6是直链或支链(C1-C20)-烷基—它是未取代的或者被相同或不同的取代基完全或部分取代,或者是(C6-C14)-芳基—它是未取代的或者被相同或不同的取代基完全或部分取代,其取代基选自(C1-C6)-烷氧基和卤素,n=0,Z是基团C-R8,其中R8是(C6-C14)-芳基—它是未取代的或者被相同或不同的取代基完全或部分取代,其取代基选自(C1-C6)-烷氧基和卤素,且X是羰基(C=O)。
按照本发明的进一方面,提供根据本发明的上述化合物用作药物。
按照本发明的进一方面,提供了根据本发明的上述化合物用于控制哺乳动物、特别是人类肿瘤病症的用途。
按照本发明的进一方面,提供药物,其包含至少一种根据本发明的上述化合物以及药学上可接受的辅助剂、稀释剂和/或载体。
按照本发明的进一方面,提供了制备根据本发明的式I化合物的方法,
其中A、B、C、D、R1、R2、R3、R4、R4、R5、X、Y、Z和n是如权利要求1所定义的,其特征在于
a)使下式酮
与aa)肟或bb)肼衍生物H2N-NH-R7反应,其中R7是如权利要求1所定义的,使所得产物与活化的羰基、亚砜或磺酰基衍生物环化,
或者与cc)苯基乙酸衍生物X1-CO-CH2-R8反应,其中X1是适合的离去基团,例如卤素或(C1-C2)-烷氧基,且R8是如权利要求1所定义,然后在碱的存在下环化。
根据本发明的式I化合物可以借助本身已知的方法得到。适合的方法例如有下述方法:
a)使具备——如果适当的话——适合的离核性离去基团E的吲哚或杂吲哚化合物与有机金属化合物反应:
其中
R1、R2、R3、R4、R5、R6、A、B、C和D是如最初所定义的,
R9是氢、直链或支链(C1-C6)-烷基羰基——它是未取代的或者被一个或多个卤原子取代、直链或支链(C1-C6)-烷氧基羰基、取代的(C6-C14)-芳基-(C1)-烷基、直链或支链(C1-C6)-烷基磺酰基或(C6-C14)-芳基磺酰基——它是未取代的或者被(C1-C6)-烷基取代,
E是OH、卤原子——例如氟、氯或溴原子、(C1-C6)-烷氧基、咪唑且M是Li、Mg-R10,
其中R10是卤原子,例如氯、溴或碘原子;
就n=0而言:
b1)使2-酰基吲哚或杂吲哚化合物与具有适合的离核性离去基团的试剂反应,如果适当的话同时或者之前除去吲哚氮原子上的取代基R9:
其中
R1、R2、R3、R4、R5、R6、R8、R9、A、B、C、D、E和X是如最初所定义的,
c1)使2-酰基吲哚或杂吲哚化合物与碱反应,优选氢化钠:
其中
R1、R2、R3、R4、R5、R6、R8、A、B、C、D和X是如最初所定义的,且Z是被基团R8取代的碳原子;
就n=1而言:
b2)使2-酰基吲哚或杂吲哚化合物与未取代的或取代的伯氨基衍生物反应:
其中
R1、R2、R3、R4、R5、R6、R9、A、B、C、D和Y是如最初所定义的,Z是氮原子,且R10是氢、直链或支链(C1-C6)-烷基、被一个或多个卤原子取代的直链或支链(C1-C6)-烷基、被一个或多个卤原子取代的直链或支链(C1-C6)-烷氧基、(C2-C6)-烯基、(C2-C6)-炔基、(C3-C8)-环烷基、(C1-C6)-烷基羰基、(C1-C6)-烷氧基羰基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C6-C14)-芳基、(C6-C14)-芳基-(C1-C6)-烷基、(C6-C14)-芳基-(C1-C6)-烷氧基-(C1-C6)-烷基、(C1-C6)-烷基羰基、(C1-C6)-烷氧基羰基,
c2)使吲哚或杂吲哚化合物与具有适合的离核性离去基团的试剂反应,如果适当的话同时或者之前除去吲哚氮原子上的取代基R9:
其中
R1、R2、R3、R4、R5、R6、R9、A、B、C、D和X是如最初所定义的,Z是氮原子,且R10是氢原子;
R11和R12彼此独立为离核性离去基团,例如卤原子,例如氯、溴或碘原子,(C1-C6)-烷氧基或N-酰咪唑(imidazolide)。
不过,这样进行制备是特别有利的,使所分离的或者原位生成的式II的吲哚或杂吲哚甲酰咪唑(heteroindolecarboximidazolide)与格利雅试剂反应,
其中
R1、R2、R3、R4、R5、R9、A、B、C和D是如最初所定义的,使式III吲哚或杂吲哚衍生物与羟胺反应,
其中
R1、R2、R3、R4、R5、R6、R9、A、B、C和D是如最初所定义的,
使式IV的吲哚或杂吲哚衍生物与N,N’-羰基二咪唑环化得到式V的吲哚或杂吲哚衍生物
其中
R1、R2、R3、R4、R5、R6、A、B、C和D是如最初所定义的,
并且在碱的存在下,例如氢化钠,使上述式III的吲哚或杂吲哚衍生物与未取代的或取代的苯基乙酰卤化物环化,得到式VI的吲哚或杂吲哚衍生物
其中
R1、R2、R3、R4、R5、R6、A、B、C和D是如最初所定义的,R9是氢原子。
用作原料的化合物有些是商业上可得到的或者是从文献中已知的,是借助从文献中已知的方法得到的;此外,在实施例中描述了其制备。从文献中已知的方法例如描述在L.and M.Fieser,OrganischeChemie[Organic Chemistry],2nd edition,1979,第1417-1483页和第1481-1483页上引用的文献;Houben-Weyl-Müller,Methodender organischen Chemie [Methods of organic chemistry]和Ullmanns Encyklopadie der technischen Chemie[Ullmann’sEncyclopedia of Technical Chemistry]中。
此外,所得式I化合物可以被分离为其对映体和/或非对映体。因而例如,以外消旋物形式存在的所得式I化合物可以借助本身已知的方法分离为其对映体,且具有至少2个不对称碳原子的式I化合物由于其物理化学差异,可以借助本身已知的方法分离为其非对映体,例如色谱法和/或分布结晶法,当得到外消旋形式时,可以如上所述分离为对映体。
对映体的分离优选地是这样进行的,借助对手性相进行柱色谱分离,或者从旋光活性的溶剂中重结晶,或者与旋光活性物质反应,后者与外消旋化合物生成盐或衍生物,例如酯或酰胺。
此外,所得式I化合物可以转化为其盐,特别是就药学应用而言,转化为其药理学上和生理学上可接受的盐,其中使用无机或有机酸。适合于这种目的的酸例如有盐酸、氢溴酸、硫酸、磷酸、富马酸、琥珀酸、乳酸、柠檬酸、酒石酸或马来酸。
而且,如果含有酸性基团,例如羧基,式I化合物能够——如果需要的话——转化为其盐,特别是就药学应用而言,转化为其生理学上可接受的盐,其中使用无机或有机碱。适合于该目的的碱例如有氢氧化钠、氢氧化钾、环己胺、乙醇胺、二乙醇胺和三乙醇胺。
下面,借助实施例详细阐述本发明;不过,本发明不限于这些实施例。
制备根据本发明的2-酰基吲哚的一般工艺
方法A)分离咪唑-1-基(1H-吲哚-2-基)甲酮并随后与有机金属试剂反应
在搅拌的同时,在室温下,历经60分钟将72mmol(11.67g,1.2当量)N,N’-羰基二咪唑的250ml四氢呋喃溶液滴加到60mmol(11.47g)5-甲氧基吲哚-2-羧酸的200ml四氢呋喃溶液中。进一步搅拌15分钟后,利用旋转蒸发器除去溶剂,使残余物从220ml四氢呋喃∶己烷=3∶2的溶液中重结晶。得到咪唑-1-基-(5-甲氧基-1H-吲哚-2-基)甲酮,为橙色-褐色固体。
M.p.:>300(分解)
在0℃下,将2.2当量有机金属化合物滴加到1当量咪唑-1-基-(5-甲氧基-1H-吲哚-2-基)甲酮的四氢呋喃溶液(3ml/mmol)中,以便内部温度不超过5℃。借助薄层色谱法监测反应的转化(移动相为乙酸乙酯∶己烷=1∶1)。反应结束后,向反应溶液加入水(10ml/mmol),用浓盐酸调节pH至6。分离有机相,水相用乙酸乙酯萃取三次(每次2ml/mmol)。合并有机相,经硫酸镁干燥,利用旋转蒸发器除去溶剂,使残余物从醇中结晶。
实施例A1:
试剂A1:氯化甲基镁,3.0M四氢呋喃溶液
1-(5-甲氧基-1H-吲哚-2-基)乙酮
M.p.:164-167℃(2-丙醇)
实施例A2:
试剂A2:溴化苯基镁,3.0M乙醚溶液
(5-甲氧基-1H-吲哚-2-基)苯基甲酮
M.p.:164-166℃(正丁醇)
实施例A3:
试剂A3:溴化3-甲氧基苯基镁,1.0M四氢呋喃溶液
(5-甲氧基-1H-吲哚-2-基)-(3-甲氧基苯基)甲酮
M.p.:143-145℃(正丁醇)
实施例A4:
试剂A4:溴化4-甲氧基苯基镁,0.5M四氢呋喃溶液
(5-甲氧基-1H-吲哚-2-基)-(4-甲氧基苯基)甲酮
M.p.:155-158℃(正丁醇)
实施例A5:
试剂A5:溴化4-氯苯基镁,1.0M乙醚溶液
(4-氯苯基)-(5-甲氧基-1H-吲哚-2-基)甲酮
M.p.:190-192℃(正丁醇)
实施例A6:
试剂A6:2-噻吩基锂,1.0M四氢呋喃溶液
(5-甲氧基-1H-吲哚-2-基)噻吩-2-基甲酮
M.p.:152-154℃(正丁醇)
方法B)一罐法:合成咪唑-1-基(1H-吲哚-2-基)甲酮并随后原位与有机金属试剂反应
在搅拌的同时,在惰性气氛下,在室温下,历经20分钟将26mmol(1.05当量)N,N’-羰基二咪唑的四氢呋喃溶液(3ml/mmol)滴加到25mmol吲哚-2-羧酸的四氢呋喃溶液(2ml/mmol)中。进一步搅拌60分钟后,将反应溶液冷却至0℃,滴加3.5当量有机金属化合物,以便内部温度不超过5℃(约60分钟)。借助薄层色谱法监测反应的转化(移动相为乙酸乙酯∶己烷=1∶1)。反应结束后,向反应溶液加入水(10ml/mmol),用浓盐酸调节pH至6。分离有机相,水相用乙酸乙酯萃取三次(每次2ml/mmol)。合并有机相,经硫酸镁干燥,利用旋转蒸发器除去溶剂,使残余物从醇中结晶。
实施例B1:
原料:吲哚-2-羧酸
试剂B1:溴化2-甲氧基苯基镁,1.0M四氢呋喃溶液
(1H-吲哚-2-基)-(2-甲氧基苯基)甲酮
M.p.:129-130℃(乙醇∶水=4∶1)
实施例B2:
原料:吲哚-2-羧酸
试剂A3:溴化3-甲氧基苯基镁,1.0M四氢呋喃溶液
(1H-吲哚-2-基)-(3-甲氧基苯基)甲酮
M.p.:119-121℃(2-丙醇)
实施例B3:
原料:5-甲氧基吲哚-2-羧酸
试剂A1:氯化甲基镁,3.0M四氢呋喃溶液
1-(5-甲氧基-1H-吲哚-2-基)乙酮
M.p.:164-167℃(2-丙醇)
实施例B4:
原料:5-甲氧基吲哚-2-羧酸
试剂B4:氯化乙基镁,3.0M四氢呋喃溶液
1-(5-甲氧基-1H-吲哚-2-基)丙-1-酮
M.p.:173-175℃(2-丙醇)
实施例B5:
原料:5-甲氧基吲哚-2-羧酸
试剂A2:溴化苯基镁,3.0M乙醚溶液
(5-甲氧基-1H-吲哚-2-基)苯基甲酮
M.p.:164-166℃(正丁醇)
实施例B6:
原料:5-甲氧基吲哚-2-羧酸
试剂A3:溴化3-甲氧基苯基镁,1.0M四氢呋喃溶液
(5-甲氧基-1H-吲哚-2-基)-(3-甲氧基苯基)甲酮
M.p.:143-145℃(正丁醇)
制备根据本发明的氧杂二氮杂(oxadiaza)衍生物的一般工艺
方法C)制备、分离和纯化吲哚-2-基肟并随后与N,N’-羰基二咪唑反应
C1)吲哚-2-基肟的一般合成:
将1.5当量固体盐酸羟胺加入到1当量根据方法A或B制备的2-酰基吲哚的乙醇悬液(10ml/mmol)中,然后在搅拌的同时,历经5分钟滴加3.0当量氢氧化钾的0.5M甲醇溶液。将反应溶液在回流下加热3-9小时(用TLC监测),冷却至室温后,倒入水中(150ml/mmol),用盐酸(10%水溶液)调节pH至6。分离所生成的沉淀,从醇/水中重结晶。如果没有沉淀生成,则分离有机相,水相用乙酸乙酯萃取三次(每次2ml/mmol),合并有机相,经硫酸镁干燥,利用旋转蒸发器除去溶剂,随后借助重结晶纯化产物,或者使粗产物按照C2(方法D)进一步反应。
实施例C1.1(D-81687):
原料A1:1-(5-甲氧基-1H-吲哚-2-基)乙酮
1-(5-甲氧基-1H-吲哚-2-基)乙酮肟
M.p.:148-150℃(2-丙醇)
实施例C1.2(D-81690):
原料B4:1-(5-甲氧基-1H-吲哚-2-基)丙-1-酮
1-(5-甲氧基-1H-吲哚-2-基)丙-1-酮肟
M.p.:163-165℃(2-丙醇)
实施例C1.3(D-70258):
原料A2:(5-甲氧基-1H-吲哚-2-基)苯基甲酮
(5-甲氧基-1H-吲哚-2-基)苯基甲酮肟
M.p.:150-152℃(2-丙醇∶水=2∶3)
实施例C1.4(D-70745):
原料A5:(4-氯苯基)-(5-甲氧基-1H-吲哚-2-基)甲酮
(4-氯苯基)-(5-甲氧基-1H-吲哚-2-基)甲酮肟
粗产物(HPLC纯度:81%)
C2)1H-吲哚-2-基甲酮肟与N,N’-羰基二咪唑的反应:
将1.2当量固体N,N’-羰基二咪唑加入到1当量1H-吲哚-2-基甲酮肟的四氢呋喃溶液(30ml/mmol)中,将混合物在回流下加热1-3小时(用TLC监测)。冷却至室温后,将反应溶液倒入水中(400ml/mmol),分离所生成的沉淀,从醇中结晶。如果没有沉淀生成,则分离有机相,水相用乙酸乙酯萃取三次(每次2ml/mmol)。合并有机相,经硫酸镁干燥,然后利用旋转蒸发器除去溶剂,产物在大气压下经过硅胶柱色谱纯化(移动相为乙酸乙酯∶己烷=1∶3)。
实施例C2.1(D-81688):
原料C1.1:1-(5-甲氧基-1H-吲哚-2-基)乙酮肟
3-甲基-1,2,5-噁二嗪并[4,5-a](5-甲氧基吲哚)-6-酮
M.p.:217-220℃(2-丙醇)
实施例C2.2(D-81691):
原料C1.2:1-(5-甲氧基-1H-吲哚-2-基)丙-1-酮肟
3-乙基-1,2,5-噁二嗪并[4,5-a](5-甲氧基吲哚)-6-酮
M.p.:208-212℃(正丁醇)
实施例C2.3(D-70260):
原料C1.3:(5-甲氧基-1H-吲哚-2-基)苯基甲酮肟
3-苯基-1,2,5-噁二嗪并[4,5-a](5-甲氧基吲哚)-6-酮
M.p.:198-200℃(正丁醇)
方法D)所制备的1H-吲哚-2-基甲酮肟直接与N,N’-羰基二咪唑反应
按照工艺C1合成下列氧杂二氮杂衍生物,但是无需纯化进一步按照C2反应。
实施例D1(D-81362):
原料B1:(1H-吲哚-2-基)-(2-甲氧基苯基)甲酮
3-(2-甲氧基苯基)-1,2,5-噁二嗪并[4,5-a]吲哚-6-酮
M.p.:160-162℃(柱色谱法)
实施例D2(D-81361):
原料B2:(1H-吲哚-2-基)-(3-甲氧基苯基)甲酮
3-(3-甲氧基苯基)-1,2,5-噁二嗪并[4,5-a]吲哚-6-酮
M.p.:129-130℃(柱色谱法)
实施例D3(D-81462):
原料A3:(5-甲氧基-1H-吲哚-2-基)-(3-甲氧基苯基)甲酮
3-(3-甲氧基苯基)-1,2,5-噁二嗪并[4,5-a](5-甲氧基吲哚)-6-酮
M.p.:171-173℃(乙醇)
实施例D4(D-70744):
原料A5:(4-氯苯基)-(5-甲氧基-1H-吲哚-2-基)甲酮
3-(4-氯苯基)-1,2,5-噁二嗪并[4,5-a](5-甲氧基吲哚)-6-酮
M.p.:227-230℃(正丁醇)
按照上述合成工艺C和D,还可以制备根据本发明的下列化合物(实施例1至324),从具有不同取代基的吲哚-2-羧酸衍生物开始:
原料:
产物(n=1,Z=N):
实施例1至324:
No. | A | C | D | R | R1 | R6 | X | Y |
1 | CH | CH | CH | H | H | CH3 | C(O) | O |
2 | CH | CH | CH | H | H | C2H5 | C(O) | O |
3 | CH | CH | CH | H | H | C6H5 | C(O) | O |
4 | CH | CH | CH | H | H | 4-(CH3O)-C6H4 | C(O) | O |
5 | CH | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | C(O) | O |
6 | CH | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | C(O) | O |
7 | CH | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | C(O) | O |
8 | CH | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | C(O) | O |
9 | CH | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | C(O) | O |
10 | C | CH | CH | 4-C6H5O | H | CH3 | C(O) | O |
11 | C | CH | CH | 4-C6H5O | H | C2H5 | C(O) | O |
12 | C | CH | CH | 4-C6H5O | H | C6H5 | C(O) | O |
13 | C | CH | CH | 4-C6H5O | H | 2-(CH3O)-C6H4 | C(O) | O |
14 | C | CH | CH | 4-C6H5O | H | 3-(CH3O)-C6H4 | C(O) | O |
15 | C | CH | CH | 4-C6H5O | H | 4-(CH3O)-C6H4 | C(O) | O |
16 | C | CH | CH | 4-C6H5O | H | 2,3-(CH3O)2-C6H3 | C(O) | O |
17 | C | CH | CH | 4-C6H5O | H | 2,4-(CH3O)2-C6H3 | C(O) | O |
18 | C | CH | CH | 4-C6H5O | H | 3,4-(CH3O)2-C6H3 | C(O) | O |
19 | C | CH | CH | 4-C6H5O | H | 3,5-(CH3O)2-C6H3 | C(O) | O |
20 | C | CH | CH | 4-C6H5O | H | 3,4,5-(CH3O)3-C6H2 | C(O) | O |
21 | CH | CH | CH | 5-CH3O | H | 2-(CH3O)-C6H4 | C(O) | O |
22 | CH | CH | CH | 5-CH3O | H | 4-(CH3O)-C6H4 | C(O) | O |
23 | CH | CH | CH | 5-CH3O | H | 2,3-(CH3O)2-C6H3 | C(O) | O |
24 | CH | CH | CH | 5-CH3O | H | 2,4-(CH3O)2-C6H3 | C(O) | O |
25 | CH | CH | CH | 5-CH3O | H | 3,4-(CH3O)2-C6H3 | C(O) | O |
26 | CH | CH | CH | 5-CH3O | H | 3,5-(CH3O)2-C6H3 | C(O) | O |
27 | CH | CH | CH | 5-CH3O | H | 3,4,5-(CH3O)3-C6H2 | C(O) | O |
28 | CH | C | CH | 6-F | H | CH3 | C(O) | O |
29 | CH | C | CH | 6-F | H | C2H5 | C(O) | O |
30 | CH | C | CH | 6-F | H | C6H5 | C(O) | O |
31 | CH | C | CH | 6-F | H | 2-(CH3O)-C6H4 | C(O) | O |
32 | CH | C | CH | 6-F | H | 3-(CH3O)-C6H4 | C(O) | O |
33 | CH | C | CH | 6-F | H | 4-(CH3O)-C6H4 | C(O) | O |
34 | CH | C | CH | 6-F | H | 2,3-(CH3O)2-C6H3 | C(O) | O |
35 | CH | C | CH | 6-F | H | 2,4-(CH3O)2-C6H3 | C(O) | O |
36 | CH | C | CH | 6-F | H | 3,4-(CH3O)2-C6H3 | C(O) | O |
37 | CH | C | CH | 6-F | H | 3,5-(CH3O)2-C6H3 | C(O) | O |
38 | CH | C | CH | 6-F | H | 3,4,5-(CH3O)3-C6H2 | C(O) | O |
39 | CH | CH | C | 7-CH3 | H | CH3 | C(O) | O |
40 | CH | CH | C | 7-CH3 | H | C2H5 | C(O) | O |
41 | CH | CH | C | 7-CH3 | H | C6H5 | C(O) | O |
42 | CH | CH | C | 7-CH3 | H | 2-(CH3O)-C6H4 | C(O) | O |
43 | CH | CH | C | 7-CH3 | H | 3-(CH3O)-C6H4 | C(O) | O |
44 | CH | CH | C | 7-CH3 | H | 4-(CH3O)-C6H4 | C(O) | O |
45 | CH | CH | C | 7-CH3 | H | 2,3-(CH3O)2-C6H3 | C(O) | O |
46 | CH | CH | C | 7-CH3 | H | 2,4-(CH3O)2-C6H3 | C(O) | O |
47 | CH | CH | C | 7-CH3 | H | 3,4-(CH3O)2-C6H3 | C(O) | O |
48 | CH | CH | C | 7-CH3 | H | 3,5-(CH3O)2-C6H3 | C(O) | O |
49 | CH | CH | C | 7-CH3 | H | 3,4,5-(CH3O)3-C6H2 | C(O) | O |
50 | CH | CH | CH | H | C6H5 | CH3 | C(O) | O |
51 | CH | CH | CH | H | C6H5 | C2H5 | C(O) | O |
52 | CH | CH | CH | H | C6H5 | C6H5 | C(O) | O |
53 | CH | CH | CH | H | C6H5 | 2-(CH3O)-C6H4 | C(O) | O |
54 | CH | CH | CH | H | C6H5 | 3-(CH3O)-C6H4 | C(O) | O |
55 | CH | CH | CH | H | C6H5 | 4-(CH3O)-C6H4 | C(O) | O |
56 | CH | CH | CH | H | C6H5 | 2,3-(CH3O)2-C6H3 | C(O) | O |
57 | CH | CH | CH | H | C6H5 | 2,4-(CH3O)2-C6H3 | C(O) | O |
58 | CH | CH | CH | H | C6H5 | 3,4-(CH3O)2-C6H3 | C(O) | O |
59 | CH | CH | CH | H | C6H5 | 3,5-(CH3O)2-C6H3 | C(O) | O |
60 | CH | CH | CH | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | C(O) | O |
61 | CH | CH | CH | 5-Cl | C6H5 | CH3 | C(O) | O |
62 | CH | CH | CH | 5-Cl | C6H5 | C2H5 | C(O) | O |
63 | CH | CH | CH | 5-Cl | C6H5 | C6H5 | C(O) | O |
64 | CH | CH | CH | 5-Cl | C6H5 | 2-(CH3O)-C6H4 | C(O) | O |
65 | CH | CH | CH | 5-Cl | C6H5 | 3-(CH3O)-C6H4 | C(O) | O |
66 | CH | CH | CH | 5-Cl | C6H5 | 4-(CH3O)-C6H4 | C(O) | O |
67 | CH | CH | CH | 5-Cl | C6H5 | 2,3-(CH3O)2-C6H3 | C(O) | O |
68 | CH | CH | CH | 5-Cl | C6H5 | 2,4-(CH3O)2-C6H3 | C(O) | O |
69 | CH | CH | CH | 5-Cl | C6H5 | 3,4-(CH3O)2-C6H3 | C(O) | O |
70 | CH | CH | CH | 5-Cl | C6H5 | 3,5-(CH3O)2-C6H3 | C(O) | O |
71 | CH | CH | CH | 5-Cl | C6H5 | 3,4,5-(CH3O)3-C6H2 | C(O) | O |
72 | N | CH | CH | H | H | CH3 | C(O) | O |
73 | N | CH | CH | H | H | C2H5 | C(O) | O |
74 | N | CH | CH | H | H | C6H5 | C(O) | O |
75 | N | CH | CH | H | H | 2-(CH3O)-C6H4 | C(O) | O |
76 | N | CH | CH | H | H | 3-(CH3O)-C6H4 | C(O) | O |
77 | N | CH | CH | H | H | 4-(CH3O)-C6H4 | C(O) | O |
78 | N | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | C(O) | O |
79 | N | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | C(O) | O |
80 | N | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | C(O) | O |
81 | N | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | C(O) | O |
82 | N | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | C(O) | O |
83 | CH | N | CH | H | H | CH3 | C(O) | O |
84 | CH | N | CH | H | H | C2H5 | C(O) | O |
85 | CH | N | CH | H | H | C6H5 | C(O) | O |
86 | CH | N | CH | H | H | 2-(CH3O)-C6H4 | C(O) | O |
87 | CH | N | CH | H | H | 3-(CH3O)-C6H4 | C(O) | O |
88 | CH | N | CH | H | H | 4-(CH3O)-C6H4 | C(O) | O |
89 | CH | N | CH | H | H | 2,3-(CH3O)2-C6H3 | C(O) | O |
90 | CH | N | CH | H | H | 2,4-(CH3O)2-C6H3 | C(O) | O |
91 | CH | N | CH | H | H | 3,4-(CH3O)2-C6H3 | C(O) | O |
92 | CH | N | CH | H | H | 3,5-(CH3O)2-C6H3 | C(O) | O |
93 | CH | N | CH | H | H | 3,4,5-(CH3O)3-C6H2 | C(O) | O |
94 | CH | CH | N | H | H | CH3 | C(O) | O |
95 | CH | CH | N | H | H | C2H5 | C(O) | O |
96 | CH | CH | N | H | H | C6H5 | C(O) | O |
97 | CH | CH | N | H | H | 2-(CH3O)-C6H4 | C(O) | O |
98 | CH | CH | N | H | H | 3-(CH3O)-C6H4 | C(O) | O |
99 | CH | CH | N | H | H | 4-(CH3O)-C6H4 | C(O) | O |
100 | CH | CH | N | H | H | 2,3-(CH3O)2-C6H3 | C(O) | O |
101 | CH | CH | N | H | H | 2,4-(CH3O)2-C6H3 | C(O) | O |
102 | CH | CH | N | H | H | 3,4-(CH3O)2-C6H3 | C(O) | O |
103 | CH | CH | N | H | H | 3,5-(CH3O)2-C6H3 | C(O) | O |
104 | CH | CH | N | H | H | 3,4,5-(CH3O)3-C6H2 | C(O) | O |
105 | CH | CH | CH | H | H | CH3 | S(O) | O |
106 | CH | CH | CH | H | H | C2H5 | S(O) | O |
107 | CH | CH | CH | H | H | C6H5 | S(O) | O |
108 | CH | CH | CH | H | H | 2-(CH3O)-C6H4 | S(O) | O |
109 | CH | CH | CH | H | H | 3-(CH3O)-C6H4 | S(O) | O |
110 | CH | CH | CH | H | H | 4-(CH3O)-C6H4 | S(O) | O |
111 | CH | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | S(O) | O |
112 | CH | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | S(O) | O |
113 | CH | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | S(O) | O |
114 | CH | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | S(O) | O |
115 | CH | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | S(O) | O |
116 | C | CH | CH | 4-C6H5O | H | CH3 | S(O) | O |
117 | C | CH | CH | 4-C6H5O | H | C2H5 | S(O) | O |
118 | C | CH | CH | 4-C6H5O | H | C6H5 | S(O) | O |
119 | C | CH | CH | 4-C6H5O | H | 2-(CH3O)-C6H4 | S(O) | O |
120 | C | CH | CH | 4-C6H5O | H | 3-(CH3O)-C6H4 | S(O) | O |
121 | C | CH | CH | 4-C6H5O | H | 4-(CH3O)-C6H4 | S(O) | O |
122 | C | CH | CH | 4-C6H5O | H | 2,3-(CH3O)2-C6H3 | S(O) | O |
123 | C | CH | CH | 4-C6H5O | H | 2,4-(CH3O)2-C6H3 | S(O) | O |
124 | C | CH | CH | 4-C6H5O | H | 3,4-(CH3O)2-C6H3 | S(O) | O |
125 | C | CH | CH | 4-C6H5O | H | 3,5-(CH3O)2-C6H3 | S(O) | O |
126 | C | CH | CH | 4-C6H5O | H | 3,4,5-(CH3O)3-C6H2 | S(O) | O |
127 | CH | CH | CH | 5-CH3O | H | CH3 | S(O) | O |
128 | CH | CH | CH | 5-CH3O | H | C2H5 | S(O) | O |
129 | CH | CH | CH | 5-CH3O | H | C6H5 | S(O) | O |
130 | CH | CH | CH | 5-CH3O | H | 2-(CH3O)-C6H4 | S(O) | O |
131 | CH | CH | CH | 5-CH3O | H | 3-(CH3O)-C6H4 | S(O) | O |
132 | CH | CH | CH | 5-CH3O | H | 4-(CH3O)-C6H4 | S(O) | O |
133 | CH | CH | CH | 5-CH3O | H | 2,3-(CH3O)2-C6H3 | S(O) | O |
134 | CH | CH | CH | 5-CH3O | H | 2,4-(CH3O)2-C6H3 | S(O) | O |
135 | CH | CH | CH | 5-CH3O | H | 3,4-(CH3O)2-C6H3 | S(O) | O |
136 | CH | CH | CH | 5-CH3O | H | 3,5-(CH3O)2-C6H3 | S(O) | O |
137 | CH | CH | CH | 5-CH3O | H | 3,4,5-(CH3O)3-C6H2 | S(O) | O |
138 | CH | C | CH | 6-F | H | CH3 | S(O) | O |
139 | CH | C | CH | 6-F | H | C2H5 | S(O) | O |
140 | CH | C | CH | 6-F | H | C6H5 | S(O) | O |
141 | CH | C | CH | 6-F | H | 2-(CH3O)-C6H4 | S(O) | O |
142 | CH | C | CH | 6-F | H | 3-(CH3O)-C6H4 | S(O) | O |
143 | CH | C | CH | 6-F | H | 4-(CH3O)-C6H4 | S(O) | O |
144 | CH | C | CH | 6-F | H | 2,3-(CH3O)2-C6H3 | S(O) | O |
145 | CH | C | CH | 6-F | H | 2,4-(CH3O)2-C6H3 | S(O) | O |
146 | CH | C | CH | 6-F | H | 3,4-(CH3O)2-C6H3 | S(O) | O |
147 | CH | C | CH | 6-F | H | 3,5-(CH3O)2-C6H3 | S(O) | O |
148 | CH | C | CH | 6-F | H | 3,4,5-(CH3O)3-C6H2 | S(O) | O |
149 | CH | CH | C | 7-CH3 | H | CH3 | S(O) | O |
150 | CH | CH | C | 7-CH3 | H | C2H5 | S(O) | O |
151 | CH | CH | C | 7-CH3 | H | C6H5 | S(O) | O |
152 | CH | CH | C | 7-CH3 | H | 2-(CH3O)-C6H4 | S(O) | O |
153 | CH | CH | C | 7-CH3 | H | 3-(CH3O)-C6H4 | S(O) | O |
154 | CH | CH | C | 7-CH3 | H | 4-(CH3O)-C6H4 | S(O) | O |
155 | CH | CH | C | 7-CH3 | H | 2,3-(CH3O)2-C6H3 | S(O) | O |
156 | CH | CH | C | 7-CH3 | H | 2,4-(CH3O)2-C6H3 | S(O) | O |
157 | CH | CH | C | 7-CH3 | H | 3,4-(CH3O)2-C6H3 | S(O) | O |
158 | CH | CH | C | 7-CH3 | H | 3,5-(CH3O)2-C6H3 | S(O) | O |
159 | CH | CH | C | 7-CH3 | H | 3,4,5-(CH3O)3-C6H2 | S(O) | O |
160 | CH | CH | CH | H | C6H5 | CH3 | S(O) | O |
161 | CH | CH | CH | H | C6H5 | C2H5 | S(O) | O |
162 | CH | CH | CH | H | C6H5 | C6H5 | S(O) | O |
163 | CH | CH | CH | H | C6H5 | 2-(CH3O)-C6H4 | S(O) | O |
164 | CH | CH | CH | H | C6H5 | 3-(CH3O)-C6H4 | S(O) | O |
165 | CH | CH | CH | H | C6H5 | 4-(CH3O)-C6H4 | S(O) | O |
166 | CH | CH | CH | H | C6H5 | 2,3-(CH3O)2-C6H3 | S(O) | O |
167 | CH | CH | CH | H | C6H5 | 2,4-(CH3O)2-C6H3 | S(O) | O |
168 | CH | CH | CH | H | C6H5 | 3,4-(CH3O)2-C6H3 | S(O) | O |
169 | CH | CH | CH | H | C6H5 | 3,5-(CH3O)2-C6H3 | S(O) | O |
170 | CH | CH | CH | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | S(O) | O |
171 | CH | CH | CH | 5-Cl | C6H5 | CH3 | S(O) | O |
172 | CH | CH | CH | 5-Cl | C6H5 | C2H5 | S(O) | O |
173 | CH | CH | CH | 5-Cl | C6H5 | C6H5 | S(O) | O |
174 | CH | CH | CH | 5-Cl | C6H5 | 2-(CH3O)-C6H4 | S(O) | O |
175 | CH | CH | CH | 5-Cl | C6H5 | 3-(CH3O)-C6H4 | S(O) | O |
176 | CH | CH | CH | 5-Cl | C6H5 | 4-(CH3O)-C6H4 | S(O) | O |
177 | CH | CH | CH | 5-Cl | C6H5 | 2,3-(CH3O)2-C6H3 | S(O) | O |
178 | CH | CH | CH | 5-Cl | C6H5 | 2,4-(CH3O)2-C6H3 | S(O) | O |
179 | CH | CH | CH | 5-Cl | C6H5 | 3,4-(CH3O)2-C6H3 | S(O) | O |
180 | CH | CH | CH | 5-Cl | C6H5 | 3,5-(CH3O)2-C6H3 | S(O) | O |
181 | CH | CH | CH | 5-Cl | C6H5 | 3,4,5-(CH3O)3-C6H2 | S(O) | O |
182 | N | CH | CH | H | H | CH3 | S(O) | O |
183 | N | CH | CH | H | H | C2H5 | S(O) | O |
184 | N | CH | CH | H | H | C6H5 | S(O) | O |
185 | N | CH | CH | H | H | 2-(CH3O)-C6H4 | S(O) | O |
186 | N | CH | CH | H | H | 3-(CH3O)-C6H4 | S(O) | O |
187 | N | CH | CH | H | H | 4-(CH3O)-C6H4 | S(O) | O |
188 | N | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | S(O) | O |
189 | N | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | S(O) | O |
190 | N | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | S(O) | O |
191 | N | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | S(O) | O |
192 | N | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | S(O) | O |
193 | CH | N | CH | H | H | CH3 | S(O) | O |
194 | CH | N | CH | H | H | C2H5 | S(O) | O |
195 | CH | N | CH | H | H | C6H5 | S(O) | O |
196 | CH | N | CH | H | H | 2-(CH3O)-C6H4 | S(O) | O |
197 | CH | N | CH | H | H | 3-(CH3O)-C6H4 | S(O) | O |
198 | CH | N | CH | H | H | 4-(CH3O)-C6H4 | S(O) | O |
199 | CH | N | CH | H | H | 2,3-(CH3O)2-C6H3 | S(O) | O |
200 | CH | N | CH | H | H | 2,4-(CH3O)2-C6H3 | S(O) | O |
201 | CH | N | CH | H | H | 3,4-(CH3O)2-C6H3 | S(O) | O |
202 | CH | N | CH | H | H | 3,5-(CH3O)2-C6H3 | S(O) | O |
203 | CH | N | CH | H | H | 3,4,5-(CH3O)3-C6H2 | S(O) | O |
204 | CH | CH | N | H | H | CH3 | S(O) | O |
205 | CH | CH | N | H | H | C2H5 | S(O) | O |
206 | CH | CH | N | H | H | C6H5 | S(O) | O |
207 | CH | CH | N | H | H | 2-(CH3O)-C6H4 | S(O) | O |
208 | CH | CH | N | H | H | 3-(CH3O)-C6H4 | S(O) | O |
209 | CH | CH | N | H | H | 4-(CH3O)-C6H4 | S(O) | O |
210 | CH | CH | N | H | H | 2,3-(CH3O)2-C6H3 | S(O) | O |
211 | CH | CH | N | H | H | 2,4-(CH3O)2-C6H3 | S(O) | O |
212 | CH | CH | N | H | H | 3,4-(CH3O)2-C6H3 | S(O) | O |
213 | CH | CH | N | H | H | 3,5-(CH3O)2-C6H3 | S(O) | O |
214 | CH | CH | N | H | H | 3,4,5-(CH3O)3-C6H2 | S(O) | O |
215 | CH | CH | CH | H | H | CH3 | SO2 | O |
216 | CH | CH | CH | H | H | C2H5 | SO2 | O |
217 | CH | CH | CH | H | H | C6H5 | SO2 | O |
218 | CH | CH | CH | H | H | 2-(CH3O)-C6H4 | SO2 | O |
219 | CH | CH | CH | H | H | 3-(CH3O)-C6H4 | SO2 | O |
220 | CH | CH | CH | H | H | 4-(CH3O)-C6H4 | SO2 | O |
221 | CH | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | SO2 | O |
222 | CH | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | SO2 | O |
223 | CH | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | SO2 | O |
224 | CH | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | SO2 | O |
225 | CH | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | SO2 | O |
226 | C | CH | CH | 4-C6H5O | H | CH3 | SO2 | O |
227 | C | CH | CH | 4-C6H5O | H | C2H5 | SO2 | O |
228 | C | CH | CH | 4-C6H5O | H | C6H5 | SO2 | O |
229 | C | CH | CH | 4-C6H5O | H | 2-(CH3O)-C6H4 | SO2 | O |
230 | C | CH | CH | 4-C6H5O | H | 3-(CH3O)-C6H4 | SO2 | O |
231 | C | CH | CH | 4-C6H5O | H | 4-(CH3O)-C6H4 | SO2 | O |
232 | C | CH | CH | 4-C6H5O | H | 2,3-(CH3O)2-C6H3 | SO2 | O |
233 | C | CH | CH | 4-C6H5O | H | 2,4-(CH3O)2-C6H3 | SO2 | O |
234 | C | CH | CH | 4-C6H5O | H | 3,4-(CH3O)2-C6H3 | SO2 | O |
235 | C | CH | CH | 4-C6H5O | H | 3,5-(CH3O)2-C6H3 | SO2 | O |
236 | C | CH | CH | 4-C6H5O | H | 3,4,5-(CH3O)3-C6H2 | SO2 | O |
237 | CH | CH | CH | 5-CH3O | H | CH3 | SO2 | O |
238 | CH | CH | CH | 5-CH3O | H | C2H5 | SO2 | O |
239 | CH | CH | CH | 5-CH3O | H | C6H5 | SO2 | O |
240 | CH | CH | CH | 5-CH3O | H | 2-(CH3O)-C6H4 | SO2 | O |
241 | CH | CH | CH | 5-CH3O | H | 3-(CH3O)-C6H4 | SO2 | O |
242 | CH | CH | CH | 5-CH3O | H | 4-(CH3O)-C6H4 | SO2 | O |
243 | CH | CH | CH | 5-CH3O | H | 2,3-(CH3O)2-C6H3 | SO2 | O |
244 | CH | CH | CH | 5-CH3O | H | 2,4-(CH3O)2-C6H3 | SO2 | O |
245 | CH | CH | CH | 5-CH3O | H | 3,4-(CH3O)2-C6H3 | SO2 | O |
246 | CH | CH | CH | 5-CH3O | H | 3,5-(CH3O)2-C6H3 | SO2 | O |
247 | CH | CH | CH | 5-CH3O | H | 3,4,5-(CH3O)3-C6H2 | SO2 | O |
248 | CH | C | CH | 6-F | H | CH3 | SO2 | O |
249 | CH | C | CH | 6-F | H | C2H5 | SO2 | O |
250 | CH | C | CH | 6-F | H | C6H5 | SO2 | O |
251 | CH | C | CH | 6-F | H | 2-(CH3O)-C6H4 | SO2 | O |
252 | CH | C | CH | 6-F | H | 3-(CH3O)-C6H4 | SO2 | O |
253 | CH | C | CH | 6-F | H | 4-(CH3O)-C6H4 | SO2 | O |
254 | CH | C | CH | 6-F | H | 2,3-(CH3O)2-C6H3 | SO2 | O |
255 | CH | C | CH | 6-F | H | 2,4-(CH3O)2-C6H3 | SO2 | O |
256 | CH | C | CH | 6-F | H | 3,4-(CH3O)2-C6H3 | SO2 | O |
257 | CH | C | CH | 6-F | H | 3,5-(CH3O)2-C6H3 | SO2 | O |
258 | CH | C | CH | 6-F | H | 3,4,5-(CH3O)3-C6H2 | SO2 | O | ||
259 | CH | CH | C | 7-CH3 | H | CH3 | SO2 | O | ||
260 | CH | CH | C | 7-CH3 | H | C2H5 | SO2 | O | ||
261 | CH | CH | C | 7-CH3 | H | C6H5 | SO2 | O | ||
262 | CH | CH | C | 7-CH3 | H | 2-(CH3O)-C6H4 | SO2 | O | ||
263 | CH | CH | C | 7-CH3 | H | 3-(CH3O)-C6H4 | SO2 | O | ||
264 | CH | CH | C | 7-CH3 | H | 4-(CH3O)-C6H4 | SO2 | O | ||
265 | CH | CH | C | 7-CH3 | H | 2,3-(CH3O)2-C6H3 | SO2 | O | ||
266 | CH | CH | C | 7-CH3 | H | 2,4-(CH3O)2-C6H3 | SO2 | O | ||
267 | CH | CH | C | 7-CH3 | H | 3,4-(CH3O)2-C6H3 | SO2 | O | ||
268 | CH | CH | C | 7-CH3 | H | 3,5-(CH3O)2-C6H3 | SO2 | O | ||
269 | CH | CH | C | 7-CH3 | H | 3,4,5-(CH3O)3-C6H2 | SO2 | O | ||
270 | CH | CH | CH | H | C6H5 | CH3 | SO2 | O | ||
271 | CH | CH | CH | H | C6H5 | C2H5 | SO2 | O | ||
272 | CH | CH | CH | H | C6H5 | C6H5 | SO2 | O | ||
273 | CH | CH | CH | H | C6H5 | 2-(CH3O)-C6H4 | SO2 | O | ||
274 | CH | CH | CH | H | C6H5 | 3-(CH3O)-C6H4 | SO2 | O | ||
275 | CH | CH | CH | H | C6H5 | 4-(CH3O)-C6H4 | SO2 | O | ||
276 | CH | CH | CH | H | C6H5 | 2,3-(CH3O)2-C6H3 | SO2 | O | ||
277 | CH | CH | CH | H | C6H5 | 2,4-(CH3O)2-C6H3 | SO2 | O | ||
278 | CH | CH | CH | H | C6H5 | 3,4-(CH3O)2-C6H3 | SO2 | O | ||
279 | CH | CH | CH | H | C6H5 | 3,5-(CH3O)2-C6H3 | SO2 | O | ||
280 | CH | CH | CH | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | SO2 | O | ||
281 | CH | CH | CH | 5-Cl | C6H5 | CH3 | SO2 | O | ||
282 | CH | CH | CH | 5-Cl | C6H5 | C2H5 | SO2 | O | ||
283 | CH | CH | CH | 5-Cl | C6H5 | C6H5 | SO2 | O | ||
284 | CH | CH | CH | 5-Cl | C6H5 | 2-(CH3O)-C6H4 | SO2 | O | ||
285 | CH | CH | CH | 5-Cl | C6H5 | 3-(CH3O)-C6H4 | SO2 | O | ||
286 | CH | CH | CH | 5-Cl | C6H5 | 4-(CH3O)-C6H4 | SO2 | O | ||
287 | CH | CH | CH | 5-Cl | C6H5 | 2,3-(CH3O)2-C6H3 | SO2 | O | ||
288 | CH | CH | CH | 5-Cl | C6H5 | 2,4-(CH3O)2-C6H3 | SO2 | O | ||
289 | CH | CH | CH | 5-Cl | C6H5 | 3,4-(CH3O)2-C6H3 | SO2 | O | ||
290 | CH | CH | CH | 5-Cl | C6H5 | 3,5-(CH3O)2-C6H3 | SO2 | O | ||
291 | CH | CH | CH | 5-Cl | C6H5 | 3,4,5-(CH3O)3-C6H2 | SO2 | O | ||
292 | N | CH | CH | H | H | CH3 | SO2 | O | ||
293 | N | CH | CH | H | H | C2H5 | SO2 | O | ||
294 | N | CH | CH | H | H | C6H5 | SO2 | O |
295 | N | CH | CH | H | H | 2-(CH3O)-C6H4 | SO2 | O |
296 | N | CH | CH | H | H | 3-(CH3O)-C6H4 | SO2 | O |
297 | N | CH | CH | H | H | 4-(CH3O)-C6H4 | SO2 | O |
298 | N | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | SO2 | O |
299 | N | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | SO2 | O |
300 | N | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | SO2 | O |
301 | N | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | SO2 | O |
302 | N | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | SO2 | O |
303 | CH | N | CH | H | H | CH3 | SO2 | O |
304 | CH | N | CH | H | H | C2H5 | SO2 | O |
305 | CH | N | CH | H | H | C6H5 | SO2 | O |
306 | CH | N | CH | H | H | 2-(CH3O)-C6H4 | SO2 | O |
307 | CH | N | CH | H | H | 3-(CH3O)-C6H4 | SO2 | O |
308 | CH | N | CH | H | H | 4-(CH3O)-C6H4 | SO2 | O |
309 | CH | N | CH | H | H | 2,3-(CH3O)2-C6H3 | SO2 | O |
310 | CH | N | CH | H | H | 2,4-(CH3O)2-C6H3 | SO2 | O |
311 | CH | N | CH | H | H | 3,4-(CH3O)2-C6H3 | SO2 | O |
312 | CH | N | CH | H | H | 3,5-(CH3O)2-C6H3 | SO2 | O |
313 | CH | N | CH | H | H | 3,4,5-(CH3O)3-C6H2 | SO2 | O |
314 | CH | CH | N | H | H | CH3 | SO2 | O |
315 | CH | CH | N | H | H | C2H5 | SO2 | O |
316 | CH | CH | N | H | H | C6H5 | SO2 | O |
317 | CH | CH | N | H | H | 2-(CH3O)-C6H4 | SO2 | O |
318 | CH | CH | N | H | H | 3-(CH3O)-C6H4 | SO2 | O |
319 | CH | CH | N | H | H | 4-(CH3O)-C6H4 | SO2 | O |
320 | CH | CH | N | H | H | 2,3-(CH3O)2-C6H3 | SO2 | O |
321 | CH | CH | N | H | H | 2,4-(CH3O)2-C6H3 | SO2 | O |
322 | CH | CH | N | H | H | 3,4-(CH3O)2-C6H3 | SO2 | O |
323 | CH | CH | N | H | H | 3,5-(CH3O)2-C6H3 | SO2 | O |
324 | CH | CH | N | H | H | 3,4,5-(CH3O)3-C6H2 | SO2 | O |
类似地,按照下面给出的一般工艺E,有可能制备根据本发明的下列化合物(实施例325至2634):
实施例325-654:
A、C、D、R、R1、R6和X具有如上实施例1-324所给出的含义,Y在每种情况下都是NH;
实施例655-984:
A、C、D、R、R1、R6和X具有如上实施例1-324所给出的含义,Y在每种情况下都是N-CH3;
实施例985-1314:
A、C、D、R、R1、R6和X具有如上实施例1-324所给出的含义,Y在每种情况下都是N-C2H5;
实施例1315-1644:
A、C、D、R、R1、R6和X具有如上实施例1-324所给出的含义,Y在每种情况下都是N-C6H5;
实施例1645-1974:
A、C、D、R、R1、R6和X具有如上实施例1-324所给出的含义,Y在每种情况下都是N-2-(CH3O)-C6H4;
实施例1975-2304:
A、C、D、R、R1、R6和X具有如上实施例1-324所给出的含义,Y在每种情况下都是N-3-(CH3O)-C6H4;
实施例2305-2634:
A、C、D、R、R1、R6和X具有如上实施例1-324所给出的含义,Y在每种情况下都是N-4-(CH3O)-C6H4。
E)制备根据本发明的1,2,4-三嗪并[4,5-a]吲哚衍生物的一般工艺
将2当量单取代的肼衍生物和冰乙酸(0.5ml/mmol)加入到1当量按照方法A或B制备的2-酰基吲哚的正丁醇悬液(10ml/mmol)中,将混合物在回流下加热16小时(用TLC监测)。冷却至室温后,将反应溶液倒入水中(150ml/mmol),分离有机相,水相用乙酸乙酯萃取三次(10ml/mmol)。合并有机相,经硫酸镁干燥,利用旋转蒸发器小心地除去溶剂,将粗产物溶于四氢呋喃(7.5ml/mmol)。向该溶液加入1.3当量N,N’-羰基二咪唑,然后加入2.1当量氢化钠(75%强度白油分散体),在室温下2小时后,将混合物在回流下加热48小时。冷却至室温后,将反应溶液倒入水中(150ml/mmol),分离固体,产物在大气压下经过硅胶柱色谱纯化(移动相为乙醚∶己烷=1∶2)。
实施例E1(D-70746):
原料A5:(4-氯苯基)-(5-甲氧基-1H-吲哚-2-基)甲酮
试剂E1:苯肼
2-苯基-6-(4-氯苯基)-1,2,4-三嗪并[4,5-a](5-甲氧基吲哚)-3-酮
M.p.:155-158℃
F)制备根据本发明的吡咯并[1,2-a]吲哚衍生物的一般工艺
将1.1当量固体氢化钠(60-75%矿物油分散体)加入到1当量按照方法A或B制备的2-酰基吲哚的N,N’-二甲基甲酰胺溶液(10ml/mmol)中,每次加入少量,在室温下搅拌5分钟后,将混合物在90℃下加热1小时。然后将混合物冷却回到室温,滴加1.1当量适当取代的苯基酰卤化物,将混合物再次在90℃下加热3至8小时(用TLC监测)。冷却至室温后,将反应溶液倒入水中(150ml/mmol),分离所生成的沉淀,在大气压下经过硅胶柱色谱纯化(移动相为乙醚∶己烷=1∶3)。
实施例F1(D-80786):
原料A5:(4-氯苯基)-(5-甲氧基-1H-吲哚-2-基)甲酮
1-(4-氯苯基)-6-甲氧基-2-苯基-3a-氮杂环戊二烯并[a]茚-3-酮M.p.:152-155℃
实施例F2(D-80815):
原料B6:(5-甲氧基-1H-吲哚-2-基)-(3-甲氧基苯基)甲酮
6-甲氧基-1-(3-甲氧基苯基)-2-苯基-3a-氮杂环戊二烯并[a]茚-3-酮
M.p.:111-113℃
实施例F3(D-80816):
原料B6:(5-甲氧基-1H-吲哚-2-基)-(3-甲氧基苯基)甲酮
6-甲氧基-1,2-双(3-甲氧基苯基)-3a-氮杂环戊二烯并[a]茚-3-酮
M.p.:112-114℃
实施例F4(D-80819):
原料A4:(5-甲氧基-1H-吲哚-2-基)-(4-甲氧基苯基)甲酮
2-(4-氟苯基)-6-甲氧基-1-(4-甲氧基苯基)-3a-氮杂环戊二烯并[a]茚-3-酮
M.p.:157-160℃
按照上述合成工艺F可以制备根据本发明的下列化合物(实施例2635至3842),从具有不同取代基的吲哚-2-羧酸衍生物开始:
原料:
产物(n=0,Z=C-R8):
No. | A | C | D | R | R1 | R6 | R8 | X |
2635 | CH | CH | CH | H | H | CH3 | CH3 | C(O) |
2636 | CH | CH | CH | H | H | CH3 | C2H5 | C(O) |
2637 | CH | CH | CH | H | H | CH3 | C6H5 | C(O) |
2638 | CH | CH | CH | H | H | CH3 | 2-(CH3O)-C6H4 | C(O) |
2639 | CH | CH | CH | H | H | CH3 | 3-(CH3O)-C6H4 | C(O) |
2640 | CH | CH | CH | H | H | CH3 | 4-(CH3O)-C6H4 | C(O) |
2641 | CH | CH | CH | H | H | CH3 | 2,3-(CH3O)2-C6H3 | C(O) |
2642 | CH | CH | CH | H | H | CH3 | 2,4-(CH3O)2-C6H3 | C(O) |
2643 | CH | CH | CH | H | H | CH3 | 3,4-(CH3O)2-C6H3 | C(O) |
2644 | CH | CH | CH | H | H | CH3 | 3,5-(CH3O)2-C6H3 | C(O) |
2645 | CH | CH | CH | H | H | CH3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2646 | CH | CH | CH | H | H | C2H5 | CH3 | C(O) |
2647 | CH | CH | CH | H | H | C2H5 | C2H5 | C(O) |
2648 | CH | CH | CH | H | H | C2H5 | C6H5 | C(O) |
2649 | CH | CH | CH | H | H | C2H5 | 2-(CH3O)-C6H4 | C(O) |
2650 | CH | CH | CH | H | H | C2H5 | 3-(CH3O)-C6H4 | C(O) |
2651 | CH | CH | CH | H | H | C2H5 | 4-(CH3O)-C6H4 | C(O) |
2652 | CH | CH | CH | H | H | C2H5 | 2,3-(CH3O)2-C6H3 | C(O) |
2653 | CH | CH | CH | H | H | C2H5 | 2,4-(CH3O)2-C6H3 | C(O) |
2654 | CH | CH | CH | H | H | C2H5 | 3,4-(CH3O)2-C6H3 | C(O) |
2655 | CH | CH | CH | H | H | C2H5 | 3,5-(CH3O)2-C6H3 | C(O) |
2656 | CH | CH | CH | H | H | C2H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2657 | CH | CH | CH | H | H | C6H5 | CH3 | C(O) |
2658 | CH | CH | CH | H | H | C6H5 | C2H5 | C(O) |
2659 | CH | CH | CH | H | H | C6H5 | C6H5 | C(O) |
2660 | CH | CH | CH | H | H | C6H5 | 2-(CH3O)-C6H4 | C(O) |
2661 | CH | CH | CH | H | H | C6H5 | 3-(CH3O)-C6H4 | C(O) |
2662 | CH | CH | CH | H | H | C6H5 | 4-(CH3O)-C6H4 | C(O) |
2663 | CH | CH | CH | H | H | C6H5 | 2,3-(CH3O)2-C6H3 | C(O) |
2664 | CH | CH | CH | H | H | C6H5 | 2,4-(CH3O)2-C6H3 | C(O) |
2665 | CH | CH | CH | H | H | C6H5 | 3,4-(CH3O)2-C6H3 | C(O) |
2666 | CH | CH | CH | H | H | C6H5 | 3,5-(CH3O)2-C6H3 | C(O) |
2667 | CH | CH | CH | H | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2668 | CH | CH | CH | H | H | 2-(CH3O)-C6H4 | CH3 | C(O) |
2669 | CH | CH | CH | H | H | 2-(CH3O)-C6H4 | C2H5 | C(O) |
2670 | CH | CH | CH | H | H | 2-(CH3O)-C6H4 | C6H5 | C(O) |
2671 | CH | CH | CH | H | H | 2-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
2672 | CH | CH | CH | H | H | 2-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
2673 | CH | CH | CH | H | H | 2-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
2674 | CH | CH | CH | H | H | 2-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
2675 | CH | CH | CH | H | H | 2-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
2676 | CH | CH | CH | H | H | 2-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
2677 | CH | CH | CH | H | H | 2-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
2678 | CH | CH | CH | H | H | 2-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2679 | CH | CH | CH | H | H | 3-(CH3O)-C6H4 | CH3 | C(O) |
2680 | CH | CH | CH | H | H | 3-(CH3O)-C6H4 | C2H5 | C(O) |
2681 | CH | CH | CH | H | H | 3-(CH3O)-C6H4 | C6H5 | C(O) |
2682 | CH | CH | CH | H | H | 3-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
2683 | CH | CH | CH | H | H | 3-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
2684 | CH | CH | CH | H | H | 3-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
2685 | CH | CH | CH | H | H | 3-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
2686 | CH | CH | CH | H | H | 3-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
2687 | CH | CH | CH | H | H | 3-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
2688 | CH | CH | CH | H | H | 3-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
2689 | CH | CH | CH | H | H | 3-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2690 | CH | CH | CH | H | H | 4-(CH3O)-C6H4 | CH3 | C(O) |
2691 | CH | CH | CH | H | H | 4-(CH3O)-C6H4 | C2H5 | C(O) |
2692 | CH | CH | CH | H | H | 4-(CH3O)-C6H4 | C6H5 | C(O) |
2693 | CH | CH | CH | H | H | 4-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
2694 | CH | CH | CH | H | H | 4-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
2695 | CH | CH | CH | H | H | 4-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
2696 | CH | CH | CH | H | H | 4-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
2697 | CH | CH | CH | H | H | 4-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
2698 | CH | CH | CH | H | H | 4-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
2699 | CH | CH | CH | H | H | 4-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
2700 | CH | CH | CH | H | H | 4-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2701 | CH | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | CH3 | C(O) |
2702 | CH | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | C2H5 | C(O) |
2703 | CH | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | C6H5 | C(O) |
2704 | CH | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
2705 | CH | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
2706 | CH | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
2707 | CH | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
2708 | CH | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
2709 | CH | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
2710 | CH | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
2711 | CH | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2712 | CH | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | CH3 | C(O) |
2713 | CH | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | C2H5 | C(O) |
2714 | CH | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | C6H5 | C(O) |
2715 | CH | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
2716 | CH | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
2717 | CH | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
2718 | CH | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
2719 | CH | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
2720 | CH | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
2721 | CH | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
2722 | CH | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2723 | CH | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | CH3 | C(O) |
2724 | CH | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | C2H5 | C(O) |
2725 | CH | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | C6H5 | C(O) |
2726 | CH | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
2727 | CH | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
2728 | CH | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
2729 | CH | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
2730 | CH | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
2731 | CH | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
2732 | CH | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
2733 | CH | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2734 | CH | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | CH3 | C(O) |
2735 | CH | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | C2H5 | C(O) |
2736 | CH | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | C6H5 | C(O) |
2737 | CH | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
2738 | CH | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
2739 | CH | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
2740 | CH | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
2741 | CH | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
2742 | CH | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
2743 | CH | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
2744 | CH | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2745 | CH | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | CH3 | C(O) |
2746 | CH | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | C2H5 | C(O) |
2747 | CH | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | C6H5 | C(O) |
2748 | CH | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 2-(CH3O)-C6H4 | C(O) |
2749 | CH | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 3-(CH3O)-C6H4 | C(O) |
2750 | CH | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 4-(CH3O)-C6H4 | C(O) |
2751 | CH | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 2,3-(CH3O)2-C6H3 | C(O) |
2752 | CH | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 2,4-(CH3O)2-C6H3 | C(O) |
2753 | CH | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 3,4-(CH3O)2-C6H3 | C(O) |
2754 | CH | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 3,5-(CH3O)2-C6H3 | C(O) |
2755 | CH | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2756 | C | CH | CH | 4-C6H5O | H | CH3 | CH3 | C(O) |
2757 | C | CH | CH | 4-C6H5O | H | CH3 | C2H5 | C(O) |
2758 | C | CH | CH | 4-C6H5O | H | CH3 | C6H5 | C(O) |
2759 | C | CH | CH | 4-C6H5O | H | CH3 | 2-(CH3O)-C6H4 | C(O) |
2760 | C | CH | CH | 4-C6H5O | H | CH3 | 3-(CH3O)-C6H4 | C(O) |
2761 | C | CH | CH | 4-C6H5O | H | CH3 | 4-(CH3O)-C6H4 | C(O) |
2762 | C | CH | CH | 4-C6H5O | H | CH3 | 2,3-(CH3O)2-C6H3 | C(O) |
2763 | C | CH | CH | 4-C6H5O | H | CH3 | 2,4-(CH3O)2-C6H3 | C(O) |
2764 | C | CH | CH | 4-C6H5O | H | CH3 | 3,4-(CH3O)2-C6H3 | C(O) |
2765 | C | CH | CH | 4-C6H5O | H | CH3 | 3,5-(CH3O)2-C6H3 | C(O) |
2766 | C | CH | CH | 4-C6H5O | H | CH3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2767 | C | CH | CH | 4-C6H5O | H | C2H5 | CH3 | C(O) |
2768 | C | CH | CH | 4-C6H5O | H | C2H5 | C2H5 | C(O) |
2769 | C | CH | CH | 4-C6H5O | H | C2H5 | C6H5 | C(O) |
2770 | C | CH | CH | 4-C6H5O | H | C2H5 | 2-(CH3O)-C6H4 | C(O) |
2771 | C | CH | CH | 4-C6H5O | H | C2H5 | 3-(CH3O)-C6H4 | C(O) |
2772 | C | CH | CH | 4-C6H5O | H | C2H5 | 4-(CH3O)-C6H4 | C(O) |
2773 | C | CH | CH | 4-C6H5O | H | C2H5 | 2,3-(CH3O)2-C6H3 | C(O) |
2774 | C | CH | CH | 4-C6H5O | H | C2H5 | 2,4-(CH3O)2-C6H3 | C(O) |
2775 | C | CH | CH | 4-C6H5O | H | C2H5 | 3,4-(CH3O)2-C6H3 | C(O) |
2776 | C | CH | CH | 4-C6H5O | H | C2H5 | 3,5-(CH3O)2-C6H3 | C(O) |
2777 | C | CH | CH | 4-C6H5O | H | C2H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2778 | C | CH | CH | 4-C6H5O | H | C6H5 | CH3 | C(O) |
2779 | C | CH | CH | 4-C6H5O | H | C6H5 | C2H5 | C(O) |
2780 | C | CH | CH | 4-C6H5O | H | C6H5 | C6H5 | C(O) |
2781 | C | CH | CH | 4-C6H5O | H | C6H5 | 2-(CH3O)-C6H4 | C(O) |
2782 | C | CH | CH | 4-C6H5O | H | C6H5 | 3-(CH3O)-C6H4 | C(O) |
2783 | C | CH | CH | 4-C6H5O | H | C6H5 | 4-(CH3O)-C6H4 | C(O) |
2784 | C | CH | CH | 4-C6H5O | H | C6H5 | 2,3-(CH3O)2-C6H3 | C(O) |
2785 | C | CH | CH | 4-C6H5O | H | C6H5 | 2,4-(CH3O)2-C6H3 | C(O) |
2786 | C | CH | CH | 4-C6H5O | H | C6H5 | 3,4-(CH3O)2-C6H3 | C(O) |
2787 | C | CH | CH | 4-C6H5O | H | C6H5 | 3,5-(CH3O)2-C6H3 | C(O) |
2788 | C | CH | CH | 4-C6H5O | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2789 | C | CH | CH | 4-C6H5O | H | 2-(CH3O)-C6H4 | CH3 | C(O) |
2790 | C | CH | CH | 4-C6H5O | H | 2-(CH3O)-C6H4 | C2H5 | C(O) |
2791 | C | CH | CH | 4-C6H5O | H | 2-(CH3O)-C6H4 | C6H5 | C(O) |
2792 | C | CH | CH | 4-C6H5O | H | 2-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
2793 | C | CH | CH | 4-C6H5O | H | 2-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
2794 | C | CH | CH | 4-C6H5O | H | 2-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
2795 | C | CH | CH | 4-C6H5O | H | 2-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
2796 | C | CH | CH | 4-C6H5O | H | 2-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
2797 | C | CH | CH | 4-C6H5O | H | 2-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
2798 | C | CH | CH | 4-C6H5O | H | 2-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
2799 | C | CH | CH | 4-C6H5O | H | 2-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2800 | C | CH | CH | 4-C6H5O | H | 3-(CH3O)-C6H4 | CH3 | C(O) |
2801 | C | CH | CH | 4-C6H5O | H | 3-(CH3O)-C6H4 | C2H5 | C(O) |
2802 | C | CH | CH | 4-C6H5O | H | 3-(CH3O)-C6H4 | C6H5 | C(O) |
2803 | C | CH | CH | 4-C6H5O | H | 3-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
2804 | C | CH | CH | 4-C6H5O | H | 3-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
2805 | C | CH | CH | 4-C6H5O | H | 3-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
2806 | C | CH | CH | 4-C6H5O | H | 3-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
2807 | C | CH | CH | 4-C6H5O | H | 3-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
2808 | C | CH | CH | 4-C6H5O | H | 3-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
2809 | C | CH | CH | 4-C6H5O | H | 3-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
2810 | C | CH | CH | 4-C6H5O | H | 3-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2811 | C | CH | CH | 4-C6H5O | H | 4-(CH3O)-C6H4 | CH3 | C(O) |
2812 | C | CH | CH | 4-C6H5O | H | 4-(CH3O)-C6H4 | C2H5 | C(O) |
2813 | C | CH | CH | 4-C6H5O | H | 4-(CH3O)-C6H4 | C6H5 | C(O) |
2814 | C | CH | CH | 4-C6H5O | H | 4-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
2815 | C | CH | CH | 4-C6H5O | H | 4-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
2816 | C | CH | CH | 4-C6H5O | H | 4-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
2817 | C | CH | CH | 4-C6H5O | H | 4-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
2818 | C | CH | CH | 4-C6H5O | H | 4-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
2819 | C | CH | CH | 4-C6H5O | H | 4-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
2820 | C | CH | CH | 4-C6H5O | H | 4-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
2821 | C | CH | CH | 4-C6H5O | H | 4-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2822 | C | CH | CH | 4-C6H5O | H | 2,3-(CH3O)2-C6H3 | CH3 | C(O) |
2823 | C | CH | CH | 4-C6H5O | H | 2,3-(CH3O)2-C6H3 | C2H5 | C(O) |
2824 | C | CH | CH | 4-C6H5O | H | 2,3-(CH3O)2-C6H3 | C6H5 | C(O) |
2825 | C | CH | CH | 4-C6H5O | H | 2,3-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
2826 | C | CH | CH | 4-C6H5O | H | 2,3-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
2827 | C | CH | CH | 4-C6H5O | H | 2,3-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
2828 | C | CH | CH | 4-C6H5O | H | 2,3-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
2829 | C | CH | CH | 4-C6H5O | H | 2,3-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
2830 | C | CH | CH | 4-C6H5O | H | 2,3-(CH3O)2-C6H5 | 3,4-(CH3O)2-C6H3 | C(O) |
2831 | C | CH | CH | 4-C6H5O | H | 2,3-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
2832 | C | CH | CH | 4-C6H5O | H | 2,3-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2833 | C | CH | CH | 4-C6H5O | H | 2,4-(CH3O)2-C6H3 | CH3 | C(O) |
2834 | C | CH | CH | 4-C6H5O | H | 2,4-(CH3O)2-C6H3 | C2H5 | C(O) |
2835 | C | CH | CH | 4-C6H5O | H | 2,4-(CH3O)2-C6H3 | C6H5 | C(O) |
2836 | C | CH | CH | 4-C6H5O | H | 2,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
2837 | C | CH | CH | 4-C6H5O | H | 2,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
2838 | C | CH | CH | 4-C6H5O | H | 2,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
2839 | C | CH | CH | 4-C6H5O | H | 2,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
2840 | C | CH | CH | 4-C6H5O | H | 2,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
2841 | C | CH | CH | 4-C6H5O | H | 2,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
2842 | C | CH | CH | 4-C6H5O | H | 2,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
2843 | C | CH | CH | 4-C6H5O | H | 2,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2844 | C | CH | CH | 4-C6H5O | H | 3,4-(CH3O)2-C6H3 | CH3 | C(O) |
2845 | C | CH | CH | 4-C6H5O | H | 3,4-(CH3O)2-C6H3 | C2H5 | C(O) |
2846 | C | CH | CH | 4-C6H5O | H | 3,4-(CH3O)2-C6H3 | C6H5 | C(O) |
2847 | C | CH | CH | 4-C6H5O | H | 3,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
2848 | C | CH | CH | 4-C6H5O | H | 3,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
2849 | C | CH | CH | 4-C6H5O | H | 3,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
2850 | C | CH | CH | 4-C6H5O | H | 3,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
2851 | C | CH | CH | 4-C6H5O | H | 3,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
2852 | C | CH | CH | 4-C6H5O | H | 3,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
2853 | C | CH | CH | 4-C6H5O | H | 3,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
2854 | C | CH | CH | 4-C6H5O | H | 3,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2855 | C | CH | CH | 4-C6H5O | H | 3,5-(CH3O)2-C6H3 | CH3 | C(O) |
2856 | C | CH | CH | 4-C6H5O | H | 3,5-(CH3O)2-C6H3 | C2H5 | C(O) |
2857 | C | CH | CH | 4-C6H5O | H | 3,5-(CH3O)2-C6H3 | C6H5 | C(O) |
2858 | C | CH | CH | 4-C6H5O | H | 3,5-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
2859 | C | CH | CH | 4-C6H5O | H | 3,5-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
2860 | C | CH | CH | 4-C6H5O | H | 3,5-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
2861 | C | CH | CH | 4-C6H5O | H | 3,5-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
2862 | C | CH | CH | 4-C6H5O | H | 3,5-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
2863 | C | CH | CH | 4-C6H5O | H | 3,5-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
2864 | C | CH | CH | 4-C6H5O | H | 3,5-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
2865 | C | CH | CH | 4-C6H5O | H | 3,5-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2866 | C | CH | CH | 4-C6H5O | H | 3,4,5-(CH3O)3-C6H2 | CH3 | C(O) |
2867 | C | CH | CH | 4-C6H5O | H | 3,4,5-(CH3O)3-C6H2 | C2H5 | C(O) |
2868 | C | CH | CH | 4-C6H5O | H | 3,4,5-(CH3O)3-C6H2 | C6H5 | C(O) |
2869 | C | CH | CH | 4-C6H5O | H | 3,4,5-(CH3O)3-C6H2 | 2-(CH3O)-C6H4 | C(O) |
2870 | C | CH | CH | 4-C6H5O | H | 3,4,5-(CH3O)3-C6H2 | 3-(CH3O)-C6H4 | C(O) |
2871 | C | CH | CH | 4-C6H5O | H | 3,4,5-(CH3O)3-C6H2 | 4-(CH3O)-C6H4 | C(O) |
2872 | C | CH | CH | 4-C6H5O | H | 3,4,5-(CH3O)3-C6H2 | 2,3-(CH3O)2-C6H3 | C(O) |
2873 | C | CH | CH | 4-C6H5O | H | 3,4,5-(CH3O)3-C6H2 | 2,4-(CH3O)2-C6H3 | C(O) |
2874 | C | CH | CH | 4-C6H5O | H | 3,4,5-(CH3O)3-C6H2 | 3,4-(CH3O)2-C6H3 | C(O) |
2875 | C | CH | CH | 4-C6H5O | H | 3,4,5-(CH3O)3-C6H2 | 3,5-(CH3O)2-C6H3 | C(O) |
2876 | C | CH | CH | 4-C6H5O | H | 3,4,5-(CH3O)3-C6H2 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2877 | CH | CH | CH | 5-CH3O | H | CH3 | CH3 | C(O) |
2878 | CH | CH | CH | 5-CH3O | H | CH3 | C2H5 | C(O) |
2879 | CH | CH | CH | 5-CH3O | H | CH3 | C6H5 | C(O) |
2880 | CH | CH | CH | 5-CH3O | H | CH3 | 2-(CH3O)-C6H4 | C(O) |
2881 | CH | CH | CH | 5-CH3O | H | CH3 | 3-(CH3O)-C6H4 | C(O) |
2882 | CH | CH | CH | 5-CH3O | H | CH3 | 4-(CH3O)-C6H4 | C(O) |
2883 | CH | CH | CH | 5-CH3O | H | CH3 | 2,3-(CH3O)2-C6H3 | C(O) |
2884 | CH | CH | CH | 5-CH3O | H | CH3 | 2,4-(CH3O)2-C6H3 | C(O) |
2885 | CH | CH | CH | 5-CH3O | H | CH3 | 3,4-(CH3O)2-C6H3 | C(O) |
2886 | CH | CH | CH | 5-CH3O | H | CH3 | 3,5-(CH3O)2-C6H3 | C(O) |
2887 | CH | CH | CH | 5-CH3O | H | CH3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2888 | CH | CH | CH | 5-CH3O | H | C2H5 | CH3 | C(O) |
2889 | CH | CH | CH | 5-CH3O | H | C2H5 | C2H5 | C(O) |
2890 | CH | CH | CH | 5-CH3O | H | C2H5 | C6H5 | C(O) |
2891 | CH | CH | CH | 5-CH3O | H | C2H5 | 2-(CH3O)-C6H4 | C(O) |
2892 | CH | CH | CH | 5-CH3O | H | C2H5 | 3-(CH3O)-C6H4 | C(O) |
2893 | CH | CH | CH | 5-CH3O | H | C2H5 | 4-(CH3O)-C6H4 | C(O) |
2894 | CH | CH | CH | 5-CH3O | H | C2H5 | 2,3-(CH3O)2-C6H3 | C(O) |
2895 | CH | CH | CH | 5-CH3O | H | C2H5 | 2,4-(CH3O)2-C6H3 | C(O) |
2896 | CH | CH | CH | 5-CH3O | H | C2H5 | 3,4-(CH3O)2-C6H3 | C(O) |
2897 | CH | CH | CH | 5-CH3O | H | C2H5 | 3,5-(CH3O)2-C6H3 | C(O) |
2898 | CH | CH | CH | 5-CH3O | H | C2H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2899 | CH | CH | CH | 5-CH3O | H | C6H5 | CH3 | C(O) |
2900 | CH | CH | CH | 5-CH3O | H | C6H5 | C2H5 | C(O) |
2901 | CH | CH | CH | 5-CH3O | H | C6H5 | C6H5 | C(O) |
2902 | CH | CH | CH | 5-CH3O | H | C6H5 | 2-(CH3O)-C6H4 | C(O) |
2903 | CH | CH | CH | 5-CH3O | H | C6H5 | 3-(CH3O)-C6H4 | C(O) |
2904 | CH | CH | CH | 5-CH3O | H | C6H5 | 4-(CH3O)-C6H4 | C(O) |
2905 | CH | CH | CH | 5-CH3O | H | C6H5 | 2,3-(CH3O)2-C6H3 | C(O) |
2906 | CH | CH | CH | 5-CH3O | H | C6H5 | 2,4-(CH3O)2-C6H3 | C(O) |
2907 | CH | CH | CH | 5-CH3O | H | C6H5 | 3,4-(CH3O)2-C6H3 | C(O) |
2908 | CH | CH | CH | 5-CH3O | H | C6H5 | 3,5-(CH3O)2-C6H3 | C(O) |
2909 | CH | CH | CH | 5-CH3O | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2910 | CH | CH | CH | 5-CH3O | H | 2-(CH3O)-C6H4 | CH3 | C(O) |
2911 | CH | CH | CH | 5-CH3O | H | 2-(CH3O)-C6H4 | C2H5 | C(O) |
2912 | CH | CH | CH | 5-CH3O | H | 2-(CH3O)-C6H4 | C6H5 | C(O) |
2913 | CH | CH | CH | 5-CH3O | H | 2-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
2914 | CH | CH | CH | 5-CH3O | H | 2-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
2915 | CH | CH | CH | 5-CH3O | H | 2-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
2916 | CH | CH | CH | 5-CH3O | H | 2-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
2917 | CH | CH | CH | 5-CH3O | H | 2-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
2918 | CH | CH | CH | 5-CH3O | H | 2-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
2919 | CH | CH | CH | 5-CH3O | H | 2-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
2920 | CH | CH | CH | 5-CH3O | H | 2-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2921 | CH | CH | CH | 5-CH3O | H | 3-(CH3O)-C6H4 | CH3 | C(O) |
2922 | CH | CH | CH | 5-CH3O | H | 3-(CH3O)-C6H4 | C2H5 | C(O) |
2923 | CH | CH | CH | 5-CH3O | H | 3-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
2924 | CH | CH | CH | 5-CH3O | H | 3-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
2925 | CH | CH | CH | 5-CH3O | H | 3-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
2926 | CH | CH | CH | 5-CH3O | H | 3-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
2927 | CH | CH | CH | 5-CH3O | H | 3-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
2928 | CH | CH | CH | 5-CH3O | H | 3-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
2929 | CH | CH | CH | 5-CH3O | H | 3-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2930 | CH | CH | CH | 5-CH3O | H | 4-(CH3O)-C6H4 | CH3 | C(O) |
2931 | CH | CH | CH | 5-CH3O | H | 4-(CH3O)-C6H4 | C2H5 | C(O) |
2932 | CH | CH | CH | 5-CH3O | H | 4-(CH3O)-C6H4 | C6H5 | C(O) |
2933 | CH | CH | CH | 5-CH3O | H | 4-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
2934 | CH | CH | CH | 5-CH3O | H | 4-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
2935 | CH | CH | CH | 5-CH3O | H | 4-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
2936 | CH | CH | CH | 5-CH3O | H | 4-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
2937 | CH | CH | CH | 5-CH3O | H | 4-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
2938 | CH | CH | CH | 5-CH3O | H | 4-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
2939 | CH | CH | CH | 5-CH3O | H | 4-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
2940 | CH | CH | CH | 5-CH3O | H | 4-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2941 | CH | CH | CH | 5-CH3O | H | 2,3-(CH3O)2-C6H3 | CH3 | C(O) |
2942 | CH | CH | CH | 5-CH3O | H | 2,3-(CH3O)2-C6H3 | C2H5 | C(O) |
2943 | CH | CH | CH | 5-CH3O | H | 2,3-(CH3O)2-C6H3 | C6H5 | C(O) |
2944 | CH | CH | CH | 5-CH3O | H | 2,3-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
2945 | CH | CH | CH | 5-CH3O | H | 2,3-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
2946 | CH | CH | CH | 5-CH3O | H | 2,3-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
2947 | CH | CH | CH | 5-CH3O | H | 2,3-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
2948 | CH | CH | CH | 5-CH3O | H | 2,3-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
2949 | CH | CH | CH | 5-CH3O | H | 2,3-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
2950 | CH | CH | CH | 5-CH3O | H | 2,3-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
2951 | CH | CH | CH | 5-CH3O | H | 2,3-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2952 | CH | CH | CH | 5-CH3O | H | 2,4-(CH3O)2-C6H3 | CH3 | C(O) |
2953 | CH | CH | CH | 5-CH3O | H | 2,4-(CH3O)2-C6H3 | C2H5 | C(O) |
2954 | CH | CH | CH | 5-CH3O | H | 2,4-(CH3O)2-C6H3 | C6H5 | C(O) |
2955 | CH | CH | CH | 5-CH3O | H | 2,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
2956 | CH | CH | CH | 5-CH3O | H | 2,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
2957 | CH | CH | CH | 5-CH3O | H | 2,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
2958 | CH | CH | CH | 5-CH3O | H | 2,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
2959 | CH | CH | CH | 5-CH3O | H | 2,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
2960 | CH | CH | CH | 5-CH3O | H | 2,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
2961 | CH | CH | CH | 5-CH3O | H | 2,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
2962 | CH | CH | CH | 5-CH3O | H | 2,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2963 | CH | CH | CH | 5-CH3O | H | 3,4-(CH3O)2-C6H3 | CH3 | C(O) |
2964 | CH | CH | CH | 5-CH3O | H | 3,4-(CH3O)2-C6H3 | C2H5 | C(O) |
2965 | CH | CH | CH | 5-CH3O | H | 3,4-(CH3O)2-C6H3 | C6H5 | C(O) |
2966 | CH | CH | CH | 5-CH3O | H | 3,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
2967 | CH | CH | CH | 5-CH3O | H | 3,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
2968 | CH | CH | CH | 5-CH3O | H | 3,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
2969 | CH | CH | CH | 5-CH3O | H | 3,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
2970 | CH | CH | CH | 5-CH3O | H | 3,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
2971 | CH | CH | CH | 5-CH3O | H | 3,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
2972 | CH | CH | CH | 5-CH3O | H | 3,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
2973 | CH | CH | CH | 5-CH3O | H | 3,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2974 | CH | CH | CH | 5-CH3O | H | 3,5-(CH3O)2-C6H3 | CH3 | C(O) |
2975 | CH | CH | CH | 5-CH3O | H | 3,5-(CH3O)2-C6H3 | C2H5 | C(O) |
2976 | CH | CH | CH | 5-CH3O | H | 3,5-(CH3O)2-C6H3 | C6H5 | C(O) |
2977 | CH | CH | CH | 5-CH3O | H | 3,5-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
2978 | CH | CH | CH | 5-CH3O | H | 3,5-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
2979 | CH | CH | CH | 5-CH3O | H | 3,5-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
2980 | CH | CH | CH | 5-CH3O | H | 3,5-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
2981 | CH | CH | CH | 5-CH3O | H | 3,5-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
2982 | CH | CH | CH | 5-CH3O | H | 3,5-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
2983 | CH | CH | CH | 5-CH3O | H | 3,5-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
2984 | CH | CH | CH | 5-CH3O | H | 3,5-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2985 | CH | CH | CH | 5-CH3O | H | 3,4,5-(CH3O)3-C6H2 | CH3 | C(O) |
2986 | CH | CH | CH | 5-CH3O | H | 3,4,5-(CH3O)3-C6H2 | C2H5 | C(O) |
2987 | CH | CH | CH | 5-CH3O | H | 3,4,5-(CH3O)3-C6H2 | C6H5 | C(O) |
2988 | CH | CH | CH | 5-CH3O | H | 3,4,5-(CH3O)3-C6H2 | 2-(CH3O)-C6H4 | C(O) |
2989 | CH | CH | CH | 5-CH3O | H | 3,4,5-(CH3O)3-C6H2 | 3-(CH3O)-C6H4 | C(O) |
2990 | CH | CH | CH | 5-CH3O | H | 3,4,5-(CH3O)3-C6H2 | 4-(CH3O)-C6H4 | C(O) |
2991 | CH | CH | CH | 5-CH3O | H | 3,4,5-(CH3O)3-C6H2 | 2,3-(CH3O)2-C6H3 | C(O) |
2992 | CH | CH | CH | 5-CH3O | H | 3,4,5-(CH3O)3-C6H2 | 2,4-(CH3O)2-C6H3 | C(O) |
2993 | CH | CH | CH | 5-CH3O | H | 3,4,5-(CH3O)3-C6H2 | 3,4-(CH3O)2-C6H3 | C(O) |
2994 | CH | CH | CH | 5-CH3O | H | 3,4,5-(CH3O)3-C6H2 | 3,5-(CH3O)2-C6H3 | C(O) |
2995 | CH | CH | CH | 5-CH3O | H | 3,4,5-(CH3O)3-C6H2 | 3,4,5-(CH3O)3-C6H2 | C(O) |
2996 | CH | C | CH | 6-F | H | CH3 | CH3 | C(O) |
2997 | CH | C | CH | 6-F | H | CH3 | C2H5 | C(O) |
2998 | CH | C | CH | 6-F | H | CH3 | C6H5 | C(O) |
2999 | CH | C | CH | 6-F | H | CH3 | 2-(CH3O)-C6H4 | C(O) |
3000 | CH | C | CH | 6-F | H | CH3 | 3-(CH3O)-C6H4 | C(O) |
3001 | CH | C | CH | 6-F | H | CH3 | 4-(CH3O)-C6H4 | C(O) |
3002 | CH | C | CH | 6-F | H | CH3 | 2,3-(CH3O)2-C6H3 | C(O) |
3003 | CH | C | CH | 6-F | H | CH3 | 2,4-(CH3O)2-C6H3 | C(O) |
3004 | CH | C | CH | 6-F | H | CH3 | 3,4-(CH3O)2-C6H3 | C(O) |
3005 | CH | C | CH | 6-F | H | CH3 | 3,5-(CH3O)2-C6H3 | C(O) |
3006 | CH | C | CH | 6-F | H | CH3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3007 | CH | C | CH | 6-F | H | C2H5 | CH3 | C(O) |
3008 | CH | C | CH | 6-F | H | C2H5 | C2H5 | C(O) |
3009 | CH | C | CH | 6-F | H | C2H5 | C6H5 | C(O) |
3010 | CH | C | CH | 6-F | H | C2H5 | 2-(CH3O)-C6H4 | C(O) |
3011 | CH | C | CH | 6-F | H | C2H5 | 3-(CH3O)-C6H4 | C(O) |
3012 | CH | C | CH | 6-F | H | C2H5 | 4-(CH3O)-C6H4 | C(O) |
3013 | CH | C | CH | 6-F | H | C2H5 | 2,3-(CH3O)2-C6H3 | C(O) |
3014 | CH | C | CH | 6-F | H | C2H5 | 2,4-(CH3O)2-C6H3 | C(O) |
3015 | CH | C | CH | 6-F | H | C2H5 | 3,4-(CH3O)2-C6H3 | C(O) |
3016 | CH | C | CH | 6-F | H | C2H5 | 3,5-(CH3O)2-C6H3 | C(O) |
3017 | CH | C | CH | 6-F | H | C2H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3018 | CH | C | CH | 6-F | H | C6H5 | CH3 | C(O) |
3019 | CH | C | CH | 6-F | H | C6H5 | C2H5 | C(O) |
3020 | CH | C | CH | 6-F | H | C6H5 | C6H5 | C(O) |
3021 | CH | C | CH | 6-F | H | C6H5 | 2-(CH3O)-C6H4 | C(O) |
3022 | CH | C | CH | 6-F | H | C6H5 | 3-(CH3O)-C6H4 | C(O) |
3023 | CH | C | CH | 6-F | H | C6H5 | 4-(CH3O)-C6H4 | C(O) |
3024 | CH | C | CH | 6-F | H | C6H5 | 2,3-(CH3O)2-C6H3 | C(O) |
3025 | CH | C | CH | 6-F | H | C6H5 | 2,4-(CH3O)2-C6H3 | C(O) |
3026 | CH | C | CH | 6-F | H | C6H5 | 3,4-(CH3O)2-C6H3 | C(O) |
3027 | CH | C | CH | 6-F | H | C6H5 | 3,5-(CH3O)2-C6H3 | C(O) |
3028 | CH | C | CH | 6-F | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3029 | CH | C | CH | 6-F | H | 2-(CH3O)-C6H4 | CH3 | C(O) |
3030 | CH | C | CH | 6-F | H | 2-(CH3O)-C6H4 | C2H5 | C(O) |
3031 | CH | C | CH | 6-F | H | 2-(CH3O)-C6H4 | C6H5 | C(O) |
3032 | CH | C | CH | 6-F | H | 2-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3033 | CH | C | CH | 6-F | H | 2-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3034 | CH | C | CH | 6-F | H | 2-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3035 | CH | C | CH | 6-F | H | 2-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3036 | CH | C | CH | 6-F | H | 2-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3037 | CH | C | CH | 6-F | H | 2-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3038 | CH | C | CH | 6-F | H | 2-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3039 | CH | C | CH | 6-F | H | 2-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3040 | CH | C | CH | 6-F | H | 3-(CH3O)-C6H4 | CH3 | C(O) |
3041 | CH | C | CH | 6-F | H | 3-(CH3O)-C6H4 | C2H5 | C(O) |
3042 | CH | C | CH | 6-F | H | 3-(CH3O)-C6H4 | C6H5 | C(O) |
3043 | CH | C | CH | 6-F | H | 3-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3044 | CH | C | CH | 6-F | H | 3-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3045 | CH | C | CH | 6-F | H | 3-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3046 | CH | C | CH | 6-F | H | 3-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3047 | CH | C | CH | 6-F | H | 3-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3048 | CH | C | CH | 6-F | H | 3-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3049 | CH | C | CH | 6-F | H | 3-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3050 | CH | C | CH | 6-F | H | 3-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3051 | CH | C | CH | 6-F | H | 4-(CH3O)-C6H4 | CH3 | C(O) |
3052 | CH | C | CH | 6-F | H | 4-(CH3O)-C6H4 | C2H5 | C(O) |
3053 | CH | C | CH | 6-F | H | 4-(CH3O)-C6H4 | C6H5 | C(O) |
3054 | CH | C | CH | 6-F | H | 4-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3055 | CH | C | CH | 6-F | H | 4-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3056 | CH | C | CH | 6-F | H | 4-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3057 | CH | C | CH | 6-F | H | 4-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3058 | CH | C | CH | 6-F | H | 4-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3059 | CH | C | CH | 6-F | H | 4-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3060 | CH | C | CH | 6-F | H | 4-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3061 | CH | C | CH | 6-F | H | 4-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3062 | CH | C | CH | 6-F | H | 2,3-(CH3O)2-C6H3 | CH3 | C(O) |
3063 | CH | C | CH | 6-F | H | 2,3-(CH3O)2-C6H3 | C2H5 | C(O) |
3064 | CH | C | CH | 6-F | H | 2,3-(CH3O)2-C6H3 | C6H5 | C(O) |
3065 | CH | C | CH | 6-F | H | 2,3-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3066 | CH | C | CH | 6-F | H | 2,3-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3067 | CH | C | CH | 6-F | H | 2,3-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3068 | CH | C | CH | 6-F | H | 2,3-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3069 | CH | C | CH | 6-F | H | 2,3-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3070 | CH | C | CH | 6-F | H | 2,3-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3071 | CH | C | CH | 6-F | H | 2,3-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3072 | CH | C | CH | 6-F | H | 2,3-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3073 | CH | C | CH | 6-F | H | 2,4-(CH3O)2-C6H3 | CH3 | C(O) |
3074 | CH | C | CH | 6-F | H | 2,4-(CH3O)2-C6H3 | C2H5 | C(O) |
3075 | CH | C | CH | 6-F | H | 2,4-(CH3O)2-C6H3 | C6H5 | C(O) |
3076 | CH | C | CH | 6-F | H | 2,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3077 | CH | C | CH | 6-F | H | 2,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3078 | CH | C | CH | 6-F | H | 2,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3079 | CH | C | CH | 6-F | H | 2,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3080 | CH | C | CH | 6-F | H | 2,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3081 | CH | C | CH | 6-F | H | 2,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3082 | CH | C | CH | 6-F | H | 2,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3083 | CH | C | CH | 6-F | H | 2,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3084 | CH | C | CH | 6-F | H | 3,4-(CH3O)2-C6H3 | CH3 | C(O) |
3085 | CH | C | CH | 6-F | H | 3,4-(CH3O)2-C6H3 | C2H5 | C(O) |
3086 | CH | C | CH | 6-F | H | 3,4-(CH3O)2-C6H3 | C6H5 | C(O) |
3087 | CH | C | CH | 6-F | H | 3,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3088 | CH | C | CH | 6-F | H | 3,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3089 | CH | C | CH | 6-F | H | 3,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3090 | CH | C | CH | 6-F | H | 3,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3091 | CH | C | CH | 6-F | H | 3,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3092 | CH | C | CH | 6-F | H | 3,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3093 | CH | C | CH | 6-F | H | 3,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3094 | CH | C | CH | 6-F | H | 3,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3095 | CH | C | CH | 6-F | H | 3,5-(CH3O)2-C6H3 | CH3 | C(O) |
3096 | CH | C | CH | 6-F | H | 3,5-(CH3O)2-C6H3 | C2H5 | C(O) |
3097 | CH | C | CH | 6-F | H | 3,5-(CH3O)2-C6H3 | C6H5 | C(O) |
3098 | CH | C | CH | 6-F | H | 3,5-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3099 | CH | C | CH | 6-F | H | 3,5-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3100 | CH | C | CH | 6-F | H | 3,5-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3101 | CH | C | CH | 6-F | H | 3,5-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3102 | CH | C | CH | 6-F | H | 3,5-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3103 | CH | C | CH | 6-F | H | 3,5-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3104 | CH | C | CH | 6-F | H | 3,5-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3105 | CH | C | CH | 6-F | H | 3,5-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3106 | CH | C | CH | 6-F | H | 3,4,5-(CH3O)3-C6H2 | CH3 | C(O) |
3107 | CH | C | CH | 6-F | H | 3,4,5-(CH3O)3-C6H2 | C2H5 | C(O) |
3108 | CH | C | CH | 6-F | H | 3,4,5-(CH3O)3-C6H2 | C6H5 | C(O) |
3109 | CH | C | CH | 6-F | H | 3,4,5-(CH3O)3-C6H2 | 2-(CH3O)-C6H4 | C(O) |
3110 | CH | C | CH | 6-F | H | 3,4,5-(CH3O)3-C6H2 | 3-(CH3O)-C6H4 | C(O) |
3111 | CH | C | CH | 6-F | H | 3,4,5-(CH3O)3-C6H2 | 4-(CH3O)-C6H4 | C(O) |
3112 | CH | C | CH | 6-F | H | 3,4,5-(CH3O)3-C6H2 | 2,3-(CH3O)2-C6H3 | C(O) |
3113 | CH | C | CH | 6-F | H | 3,4,5-(CH3O)3-C6H2 | 2,4-(CH3O)2-C6H3 | C(O) |
3114 | CH | C | CH | 6-F | H | 3,4,5-(CH3O)3-C6H2 | 3,4-(CH3O)2-C6H3 | C(O) |
3115 | CH | C | CH | 6-F | H | 3,4,5-(CH3O)3-C6H2 | 3,5-(CH3O)2-C6H3 | C(O) |
3116 | CH | C | CH | 6-F | H | 3,4,5-(CH3O)3-C6H2 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3117 | CH | CH | C | 7-CH3 | H | CH3 | CH3 | C(O) |
3118 | CH | CH | C | 7-CH3 | H | CH3 | C2H5 | C(O) |
3119 | CH | CH | C | 7-CH3 | H | CH3 | C6H5 | C(O) |
3120 | CH | CH | C | 7-CH3 | H | CH3 | 2-(CH3O)-C6H4 | C(O) |
3121 | CH | CH | C | 7-CH3 | H | CH3 | 3-(CH3O)-C6H4 | C(O) |
3122 | CH | CH | C | 7-CH3 | H | CH3 | 4-(CH3O)-C6H4 | C(O) |
3123 | CH | CH | C | 7-CH3 | H | CH3 | 2,3-(CH3O)2-C6H3 | C(O) |
3124 | CH | CH | C | 7-CH3 | H | CH3 | 2,4-(CH3O)2-C6H3 | C(O) |
3125 | CH | CH | C | 7-CH3 | H | CH3 | 3,4-(CH3O)2-C6H3 | C(O) |
3126 | CH | CH | C | 7-CH3 | H | CH3 | 3,5-(CH3O)2-C6H3 | C(O) |
3127 | CH | CH | C | 7-CH3 | H | CH3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3128 | CH | CH | C | 7-CH3 | H | C2H5 | CH3 | C(O) |
3129 | CH | CH | C | 7-CH3 | H | C2H5 | C2H5 | C(O) |
3130 | CH | CH | C | 7-CH3 | H | C2H5 | C6H5 | C(O) |
3131 | CH | CH | C | 7-CH3 | H | C2H5 | 2-(CH3O)-C6H4 | C(O) |
3132 | CH | CH | C | 7-CH3 | H | C2H5 | 3-(CH3O)-C6H4 | C(O) |
3133 | CH | CH | C | 7-CH3 | H | C2H5 | 4-(CH3O)-C6H4 | C(O) |
3134 | CH | CH | C | 7-CH3 | H | C2H5 | 2,3-(CH3O)2-C6H3 | C(O) |
3135 | CH | CH | C | 7-CH3 | H | C2H5 | 2,4-(CH3O)2-C6H3 | C(O) |
3136 | CH | CH | C | 7-CH3 | H | C2H5 | 3,4-(CH3O)2-C6H3 | C(O) |
3137 | CH | CH | C | 7-CH3 | H | C2H5 | 3,5-(CH3O)2-C6H3 | C(O) |
3138 | CH | CH | C | 7-CH3 | H | C2H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3139 | CH | CH | C | 7-CH3 | H | C6H5 | CH3 | C(O) |
3140 | CH | CH | C | 7-CH3 | H | C6H5 | C2H5 | C(O) |
3141 | CH | CH | C | 7-CH3 | H | C6H5 | C6H5 | C(O) |
3142 | CH | CH | C | 7-CH3 | H | C6H5 | 2-(CH3O)-C6H4 | C(O) |
3143 | CH | CH | C | 7-CH3 | H | C6H5 | 3-(CH3O)-C6H4 | C(O) |
3144 | CH | CH | C | 7-CH3 | H | C6H5 | 4-(CH3O)-C6H4 | C(O) |
3145 | CH | CH | C | 7-CH3 | H | C6H5 | 2,3-(CH3O)2-C6H3 | C(O) |
3146 | CH | CH | C | 7-CH3 | H | C6H5 | 2,4-(CH3O)2-C6H3 | C(O) |
3147 | CH | CH | C | 7-CH3 | H | C6H5 | 3,4-(CH3O)2-C6H3 | C(O) |
3148 | CH | CH | C | 7-CH3 | H | C6H5 | 3,5-(CH3O)2-C6H3 | C(O) |
3149 | CH | CH | C | 7-CH3 | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3150 | CH | CH | C | 7-CH3 | H | 2-(CH3O)-C6H4 | CH3 | C(O) |
3151 | CH | CH | C | 7-CH3 | H | 2-(CH3O)-C6H4 | C2H5 | C(O) |
3152 | CH | CH | C | 7-CH3 | H | 2-(CH3O)-C6H4 | C6H5 | C(O) |
3153 | CH | CH | C | 7-CH3 | H | 2-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3154 | CH | CH | C | 7-CH3 | H | 2-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3155 | CH | CH | C | 7-CH3 | H | 2-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3156 | CH | CH | C | 7-CH3 | H | 2-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3157 | CH | CH | C | 7-CH3 | H | 2-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3158 | CH | CH | C | 7-CH3 | H | 2-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3159 | CH | CH | C | 7-CH3 | H | 2-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3160 | CH | CH | C | 7-CH3 | H | 2-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3161 | CH | CH | C | 7-CH3 | H | 3-(CH3O)-C6H4 | CH3 | C(O) |
3162 | CH | CH | C | 7-CH3 | H | 3-(CH3O)-C6H4 | C2H5 | C(O) |
3163 | CH | CH | C | 7-CH3 | H | 3-(CH3O)-C6H4 | C6H5 | C(O) |
3164 | CH | CH | C | 7-CH3 | H | 3-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3165 | CH | CH | C | 7-CH3 | H | 3-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3166 | CH | CH | C | 7-CH3 | H | 3-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3167 | CH | CH | C | 7-CH3 | H | 3-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3168 | CH | CH | C | 7-CH3 | H | 3-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3169 | CH | CH | C | 7-CH3 | H | 3-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3170 | CH | CH | C | 7-CH3 | H | 3-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3171 | CH | CH | C | 7-CH3 | H | 3-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3172 | CH | CH | C | 7-CH3 | H | 4-(CH3O)-C6H4 | CH3 | C(O) |
3173 | CH | CH | C | 7-CH3 | H | 4-(CH3O)-C6H4 | C2H5 | C(O) |
3174 | CH | CH | C | 7-CH3 | H | 4-(CH3O)-C6H4 | C6H5 | C(O) |
3175 | CH | CH | C | 7-CH3 | H | 4-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3176 | CH | CH | C | 7-CH3 | H | 4-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3177 | CH | CH | C | 7-CH3 | H | 4-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3178 | CH | CH | C | 7-CH3 | H | 4-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3179 | CH | CH | C | 7-CH3 | H | 4-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3180 | CH | CH | C | 7-CH3 | H | 4-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3181 | CH | CH | C | 7-CH3 | H | 4-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3182 | CH | CH | C | 7-CH3 | H | 4-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3183 | CH | CH | C | 7-CH3 | H | 2,3-(CH3O)2-C6H3 | CH3 | C(O) |
3184 | CH | CH | C | 7-CH3 | H | 2,3-(CH3O)2-C6H3 | C2H5 | C(O) |
3185 | CH | CH | C | 7-CH3 | H | 2,3-(CH3O)2-C6H3 | C6H5 | C(O) |
3186 | CH | CH | C | 7-CH3 | H | 2,3-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3187 | CH | CH | C | 7-CH3 | H | 2,3-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3188 | CH | CH | C | 7-CH3 | H | 2,3-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3189 | CH | CH | C | 7-CH3 | H | 2,3-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3190 | CH | CH | C | 7-CH3 | H | 2,3-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3191 | CH | CH | C | 7-CH3 | H | 2,3-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3192 | CH | CH | C | 7-CH3 | H | 2,3-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3193 | CH | CH | C | 7-CH3 | H | 2,3-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3194 | CH | CH | C | 7-CH3 | H | 2,4-(CH3O)2-C6H3 | CH3 | C(O) |
3195 | CH | CH | C | 7-CH3 | H | 2,4-(CH3O)2-C6H3 | C2H5 | C(O) |
3196 | CH | CH | C | 7-CH3 | H | 2,4-(CH3O)2-C6H3 | C6H5 | C(O) |
3197 | CH | CH | C | 7-CH3 | H | 2,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3198 | CH | CH | C | 7-CH3 | H | 2,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3199 | CH | CH | C | 7-CH3 | H | 2,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3200 | CH | CH | C | 7-CH3 | H | 2,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3201 | CH | CH | C | 7-CH3 | H | 2,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3202 | CH | CH | C | 7-CH3 | H | 2,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3203 | CH | CH | C | 7-CH3 | H | 2,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3204 | CH | CH | C | 7-CH3 | H | 2,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3205 | CH | CH | C | 7-CH3 | H | 3,4-(CH3O)2-C6H3 | CH3 | C(O) |
3206 | CH | CH | C | 7-CH3 | H | 3,4-(CH3O)2-C6H3 | C2H5 | C(O) |
3207 | CH | CH | C | 7-CH3 | H | 3,4-(CH3O)2-C6H3 | C6H5 | C(O) |
3208 | CH | CH | C | 7-CH3 | H | 3,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3209 | CH | CH | C | 7-CH3 | H | 3,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3210 | CH | CH | C | 7-CH3 | H | 3,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3211 | CH | CH | C | 7-CH3 | H | 3,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3212 | CH | CH | C | 7-CH3 | H | 3,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3213 | CH | CH | C | 7-CH3 | H | 3,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3214 | CH | CH | C | 7-CH3 | H | 3,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3215 | CH | CH | C | 7-CH3 | H | 3,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3216 | CH | CH | C | 7-CH3 | H | 3,5-(CH3O)2-C6H3 | CH3 | C(O) |
3217 | CH | CH | C | 7-CH3 | H | 3,5-(CH3O)2-C6H3 | C2H5 | C(O) |
3218 | CH | CH | C | 7-CH3 | H | 3,5-(CH3O)2-C6H3 | C6H5 | C(O) |
3219 | CH | CH | C | 7-CH3 | H | 3,5-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3220 | CH | CH | C | 7-CH3 | H | 3,5-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3221 | CH | CH | C | 7-CH3 | H | 3,5-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3222 | CH | CH | C | 7-CH3 | H | 3,5-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3223 | CH | CH | C | 7-CH3 | H | 3,5-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3224 | CH | CH | C | 7-CH3 | H | 3,5-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3225 | CH | CH | C | 7-CH3 | H | 3,5-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3226 | CH | CH | C | 7-CH3 | H | 3,5-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3227 | CH | CH | C | 7-CH3 | H | 3,4,5-(CH3O)3-C6H2 | CH3 | C(O) |
3228 | CH | CH | C | 7-CH3 | H | 3,4,5-(CH3O)3-C6H2 | C2H5 | C(O) |
3229 | CH | CH | C | 7-CH3 | H | 3,4,5-(CH3O)3-C6H2 | C6H5 | C(O) |
3230 | CH | CH | C | 7-CH3 | H | 3,4,5-(CH3O)3-C6H2 | 2-(CH3O)-C6H4 | C(O) |
3231 | CH | CH | C | 7-CH3 | H | 3,4,5-(CH3O)3-C6H2 | 3-(CH3O)-C6H4 | C(O) |
3232 | CH | CH | C | 7-CH3 | H | 3,4,5-(CH3O)3-C6H2 | 4-(CH3O)-C6H4 | C(O) |
3233 | CH | CH | C | 7-CH3 | H | 3,4,5-(CH3O)3-C6H2 | 2,3-(CH3O)2-C6H3 | C(O) |
3234 | CH | CH | C | 7-CH3 | H | 3,4,5-(CH3O)3-C6H2 | 2,4-(CH3O)2-C6H3 | C(O) |
3235 | CH | CH | C | 7-CH3 | H | 3,4,5-(CH3O)3-C6H2 | 3,4-(CH3O)2-C6H3 | C(O) |
3236 | CH | CH | C | 7-CH3 | H | 3,4,5-(CH3O)3-C6H2 | 3,5-(CH3O)2-C6H3 | C(O) |
3237 | CH | CH | C | 7-CH3 | H | 3,4,5-(CH3O)3-C6H2 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3238 | CH | CH | CH | H | C6H5 | CH3 | CH3 | C(O) |
3239 | CH | CH | CH | H | C6H5 | CH3 | C2H5 | C(O) |
3240 | CH | CH | CH | H | C6H5 | CH3 | C6H5 | C(O) |
3241 | CH | CH | CH | H | C6H5 | CH3 | 2-(CH3O)-C6H4 | C(O) |
3242 | CH | CH | CH | H | C6H5 | CH3 | 3-(CH3O)-C6H4 | C(O) |
3243 | CH | CH | CH | H | C6H5 | CH3 | 4-(CH3O)-C6H4 | C(O) |
3244 | CH | CH | CH | H | C6H5 | CH3 | 2,3-(CH3O)2-C6H3 | C(O) |
3245 | CH | CH | CH | H | C6H5 | CH3 | 2,4-(CH3O)2-C6H3 | C(O) |
3246 | CH | CH | CH | H | C6H5 | CH3 | 3,4-(CH3O)2-C6H3 | C(O) |
3247 | CH | CH | CH | H | C6H5 | CH3 | 3,5-(CH3O)2-C6H3 | C(O) |
3248 | CH | CH | CH | H | C6H5 | CH3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3249 | CH | CH | CH | H | C6H5 | C2H5 | CH3 | C(O) |
3250 | CH | CH | CH | H | C6H5 | C2H5 | C2H5 | C(O) |
3251 | CH | CH | CH | H | C6H5 | C2H5 | C6H5 | C(O) |
3252 | CH | CH | CH | H | C6H5 | C2H5 | 2-(CH3O)-C6H4 | C(O) |
3253 | CH | CH | CH | H | C6H5 | C2H5 | 3-(CH3O)-C6H4 | C(O) |
3254 | CH | CH | CH | H | C6H5 | C2H5 | 4-(CH3O)-C6H4 | C(O) |
3255 | CH | CH | CH | H | C6H5 | C2H5 | 2,3-(CH3O)2-C6H3 | C(O) |
3256 | CH | CH | CH | H | C6H5 | C2H5 | 2,4-(CH3O)2-C6H3 | C(O) |
3257 | CH | CH | CH | H | C6H5 | C2H5 | 3,4-(CH3O)2-C6H3 | C(O) |
3258 | CH | CH | CH | H | C6H5 | C2H5 | 3,5-(CH3O)2-C6H3 | C(O) |
3259 | CH | CH | CH | H | C6H5 | C2H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3260 | CH | CH | CH | H | C6H5 | C6H5 | CH3 | C(O) |
3261 | CH | CH | CH | H | C6H5 | C6H5 | C2H5 | C(O) |
3262 | CH | CH | CH | H | C6H5 | C6H5 | C6H5 | C(O) |
3263 | CH | CH | CH | H | C6H5 | C6H5 | 2-(CH3O)-C6H4 | C(O) |
3264 | CH | CH | CH | H | C6H5 | C6H5 | 3-(CH3O)-C6H4 | C(O) |
3265 | CH | CH | CH | H | C6H5 | C6H5 | 4-(CH3O)-C6H4 | C(O) |
3266 | CH | CH | CH | H | C6H5 | C6H5 | 2,3-(CH3O)2-C6H3 | C(O) |
3267 | CH | CH | CH | H | C6H5 | C6H5 | 2,4-(CH3O)2-C6H3 | C(O) |
3268 | CH | CH | CH | H | C6H5 | C6H5 | 3,4-(CH3O)2-C6H3 | C(O) |
3269 | CH | CH | CH | H | C6H5 | C6H5 | 3,5-(CH3O)2-C6H3 | C(O) |
3270 | CH | CH | CH | H | C6H5 | C6H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3271 | CH | CH | CH | H | C6H5 | 2-(CH3O)-C6H4 | CH3 | C(O) |
3272 | CH | CH | CH | H | C6H5 | 2-(CH3O)-C6H4 | C2H5 | C(O) |
3273 | CH | CH | CH | H | C6H5 | 2-(CH3O)-C6H4 | C6H5 | C(O) |
3274 | CH | CH | CH | H | C6H5 | 2-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3275 | CH | CH | CH | H | C6H5 | 2-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3276 | CH | CH | CH | H | C6H5 | 2-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3277 | CH | CH | CH | H | C6H5 | 2-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3278 | CH | CH | CH | H | C6H5 | 2-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3279 | CH | CH | CH | H | C6H5 | 2-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3280 | CH | CH | CH | H | C6H5 | 2-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3281 | CH | CH | CH | H | C6H5 | 2-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3282 | CH | CH | CH | H | C6H5 | 3-(CH3O)-C6H4 | CH3 | C(O) |
3283 | CH | CH | CH | H | C6H5 | 3-(CH3O)-C6H4 | C2H5 | C(O) |
3284 | CH | CH | CH | H | C6H5 | 3-(CH3O)-C6H4 | C6H5 | C(O) |
3285 | CH | CH | CH | H | C6H5 | 3-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3286 | CH | CH | CH | H | C6H5 | 3-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3287 | CH | CH | CH | H | C6H5 | 3-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3288 | CH | CH | CH | H | C6H5 | 3-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3289 | CH | CH | CH | H | C6H5 | 3-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3290 | CH | CH | CH | H | C6H5 | 3-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3291 | CH | CH | CH | H | C6H5 | 3-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3292 | CH | CH | CH | H | C6H5 | 3-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3293 | CH | CH | CH | H | C6H5 | 4-(CH3O)-C6H4 | CH3 | C(O) |
3294 | CH | CH | CH | H | C6H5 | 4-(CH3O)-C6H4 | C2H5 | C(O) |
3295 | CH | CH | CH | H | C6H5 | 4-(CH3O)-C6H4 | C6H5 | C(O) |
3296 | CH | CH | CH | H | C6H5 | 4-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3297 | CH | CH | CH | H | C6H5 | 4-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3298 | CH | CH | CH | H | C6H5 | 4-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3299 | CH | CH | CH | H | C6H5 | 4-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3300 | CH | CH | CH | H | C6H5 | 4-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3301 | CH | CH | CH | H | C6H5 | 4-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3302 | CH | CH | CH | H | C6H5 | 4-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3303 | CH | CH | CH | H | C6H5 | 4-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3304 | CH | CH | CH | H | C6H5 | 2,3-(CH3O)2-C6H3 | CH3 | C(O) |
3305 | CH | CH | CH | H | C6H5 | 2,3-(CH3O)2-C6H3 | C2H5 | C(O) |
3306 | CH | CH | CH | H | C6H5 | 2,3-(CH3O)2-C6H3 | C6H5 | C(O) |
3307 | CH | CH | CH | H | C6H5 | 2,3-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3308 | CH | CH | CH | H | C6H5 | 2,3-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3309 | CH | CH | CH | H | C6H5 | 2,3-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3310 | CH | CH | CH | H | C6H5 | 2,3-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3311 | CH | CH | CH | H | C6H5 | 2,3-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3312 | CH | CH | CH | H | C6H5 | 2,3-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3313 | CH | CH | CH | H | C6H5 | 2,3-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3314 | CH | CH | CH | H | C6H5 | 2,3-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3315 | CH | CH | CH | H | C6H5 | 2,4-(CH3O)2-C6H3 | CH3 | C(O) |
3316 | CH | CH | CH | H | C6H5 | 2,4-(CH3O)2-C6H3 | C2H5 | C(O) |
3317 | CH | CH | CH | H | C6H5 | 2,4-(CH3O)2-C6H3 | C6H5 | C(O) |
3318 | CH | CH | CH | H | C6H5 | 2,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3319 | CH | CH | CH | H | C6H5 | 2,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3320 | CH | CH | CH | H | C6H5 | 2,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3321 | CH | CH | CH | H | C6H5 | 2,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3322 | CH | CH | CH | H | C6H5 | 2,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3323 | CH | CH | CH | H | C6H5 | 2,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3324 | CH | CH | CH | H | C6H5 | 2,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3325 | CH | CH | CH | H | C6H5 | 2,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3326 | CH | CH | CH | H | C6H5 | 3,4-(CH3O)2-C6H3 | CH3 | C(O) |
3327 | CH | CH | CH | H | C6H5 | 3,4-(CH3O)2-C6H3 | C2H5 | C(O) |
3328 | CH | CH | CH | H | C6H5 | 3,4-(CH3O)2-C6H3 | C6H5 | C(O) |
3329 | CH | CH | CH | H | C6H5 | 3,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3330 | CH | CH | CH | H | C6H5 | 3,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3331 | CH | CH | CH | H | C6H5 | 3,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3332 | CH | CH | CH | H | C6H5 | 3,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3333 | CH | CH | CH | H | C6H5 | 3,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3334 | CH | CH | CH | H | C6H5 | 3,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3335 | CH | CH | CH | H | C6H5 | 3,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3336 | CH | CH | CH | H | C6H5 | 3,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3337 | CH | CH | CH | H | C6H5 | 3,5-(CH3O)2-C6H3 | CH3 | C(O) |
3338 | CH | CH | CH | H | C6H5 | 3,5-(CH3O)2-C6H3 | C2H5 | C(O) |
3339 | CH | CH | CH | H | C6H5 | 3,5-(CH3O)2-C6H3 | C6H5 | C(O) |
3340 | CH | CH | CH | H | C6H5 | 3,5-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3341 | CH | CH | CH | H | C6H5 | 3,5-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3342 | CH | CH | CH | H | C6H5 | 3,5-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3343 | CH | CH | CH | H | C6H5 | 3,5-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3344 | CH | CH | CH | H | C6H5 | 3,5-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3345 | CH | CH | CH | H | C6H5 | 3,5-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3346 | CH | CH | CH | H | C6H5 | 3,5-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3347 | CH | CH | CH | H | C6H5 | 3,5-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3348 | CH | CH | CH | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | CH3 | C(O) |
3349 | CH | CH | CH | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | C2H5 | C(O) |
3350 | CH | CH | CH | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | C6H5 | C(O) |
3351 | CH | CH | CH | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | 2-(CH3O)-C6H4 | C(O) |
3352 | CH | CH | CH | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | 3-(CH3O)-C6H4 | C(O) |
3353 | CH | CH | CH | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | 4-(CH3O)-C6H4 | C(O) |
3354 | CH | CH | CH | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | 2,3-(CH3O)2-C6H3 | C(O) |
3355 | CH | CH | CH | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | 2,4-(CH3O)2-C6H3 | C(O) |
3356 | CH | CH | CH | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | 3,4-(CH3O)2-C6H3 | C(O) |
3357 | CH | CH | CH | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | 3,5-(CH3O)2-C6H3 | C(O) |
3358 | CH | CH | CH | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3359 | CH | CH | CH | 5-Cl | C6H5 | CH3 | CH3 | C(O) |
3360 | CH | CH | CH | 5-Cl | C6H5 | CH3 | C2H5 | C(O) |
3361 | CH | CH | CH | 5-Cl | C6H5 | CH3 | C6H5 | C(O) |
3362 | CH | CH | CH | 5-Cl | C6H5 | CH3 | 2-(CH3O)-C6H4 | C(O) |
3363 | CH | CH | CH | 5-Cl | C6H5 | CH3 | 3-(CH3O)-C6H4 | C(O) |
3364 | CH | CH | CH | 5-Cl | C6H5 | CH3 | 4-(CH3O)-C6H4 | C(O) |
3365 | CH | CH | CH | 5-Cl | C6H5 | CH3 | 2,3-(CH3O)2-C6H3 | C(O) |
3366 | CH | CH | CH | 5-Cl | C6H5 | CH3 | 2,4-(CH3O)2-C6H3 | C(O) |
3367 | CH | CH | CH | 5-Cl | C6H5 | CH3 | 3,4-(CH3O)2-C6H3 | C(O) |
3368 | CH | CH | CH | 5-Cl | C6H5 | CH3 | 3,5-(CH3O)2-C6H3 | C(O) |
3369 | CH | CH | CH | 5-Cl | C6H5 | CH3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3370 | CH | CH | CH | 5-Cl | C6H5 | C2H5 | CH3 | C(O) |
3371 | CH | CH | CH | 5-Cl | C6H5 | C2H5 | C2H5 | C(O) |
3372 | CH | CH | CH | 5-Cl | C6H5 | C2H5 | C6H5 | C(O) |
3373 | CH | CH | CH | 5-Cl | C6H5 | C2H5 | 2-(CH3O)-C6H4 | C(O) |
3374 | CH | CH | CH | 5-Cl | C6H5 | C2H5 | 3-(CH3O)-C6H4 | C(O) |
3375 | CH | CH | CH | 5-Cl | C6H5 | C2H5 | 4-(CH3O)-C6H4 | C(O) |
3376 | CH | CH | CH | 5-Cl | C6H5 | C2H5 | 2,3-(CH3O)2-C6H3 | C(O) |
3377 | CH | CH | CH | 5-Cl | C6H5 | C2H5 | 2,4-(CH3O)2-C6H3 | C(O) |
3378 | CH | CH | CH | 5-Cl | C6H5 | C2H5 | 3,4-(CH3O)2-C6H3 | C(O) |
3379 | CH | CH | CH | 5-Cl | C6H5 | C2H5 | 3,5-(CH3O)2-C6H3 | C(O) |
3380 | CH | CH | CH | 5-Cl | C6H5 | C2H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3381 | CH | CH | CH | 5-Cl | C6H5 | C6H5 | CH3 | C(O) |
3382 | CH | CH | CH | 5-Cl | C6H5 | C6H5 | C2H5 | C(O) |
3383 | CH | CH | CH | 5-Cl | C6H5 | C6H5 | C6H5 | C(O) |
3384 | CH | CH | CH | 5-Cl | C6H5 | C6H5 | 2-(CH3O)-C6H4 | C(O) |
3385 | CH | CH | CH | 5-Cl | C6H5 | C6H5 | 3-(CH3O)-C6H4 | C(O) |
3386 | CH | CH | CH | 5-Cl | C6H5 | C6H5 | 4-(CH3O)-C6H4 | C(O) |
3387 | CH | CH | CH | 5-Cl | C6H5 | C6H5 | 2,3-(CH3O)2-C6H3 | C(O) |
3388 | CH | CH | CH | 5-Cl | C6H5 | C6H5 | 2,4-(CH3O)2-C6H3 | C(O) |
3389 | CH | CH | CH | 5-Cl | C6H5 | C6H5 | 3,4-(CH3O)2-C6H3 | C(O) |
3390 | CH | CH | CH | 5-Cl | C6H5 | C6H5 | 3,5-(CH3O)2-C6H3 | C(O) |
3391 | CH | CH | CH | 5-Cl | C6H5 | C6H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3392 | CH | CH | CH | 5-Cl | C6H5 | 2-(CH3O)-C6H4 | CH3 | C(O) |
3393 | CH | CH | CH | 5-Cl | C6H5 | 2-(CH3O)-C6H4 | C2H5 | C(O) |
3394 | CH | CH | CH | 5-Cl | C6H5 | 2-(CH3O)-C6H4 | C6H5 | C(O) |
3395 | CH | CH | CH | 5-Cl | C6H5 | 2-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3396 | CH | CH | CH | 5-Cl | C6H5 | 2-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3397 | CH | CH | CH | 5-Cl | C6H5 | 2-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3398 | CH | CH | CH | 5-Cl | C6H5 | 2-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3399 | CH | CH | CH | 5-Cl | C6H5 | 2-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3400 | CH | CH | CH | 5-Cl | C6H5 | 2-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3401 | CH | CH | CH | 5-Cl | C6H5 | 2-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3402 | CH | CH | CH | 5-Cl | C6H5 | 2-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3403 | CH | CH | CH | 5-Cl | C6H5 | 3-(CH3O)-C6H4 | CH3 | C(O) |
3404 | CH | CH | CH | 5-Cl | C6H5 | 3-(CH3O)-C6H4 | C2H5 | C(O) |
3405 | CH | CH | CH | 5-Cl | C6H5 | 3-(CH3O)-C6H4 | C6H5 | C(O) |
3406 | CH | CH | CH | 5-Cl | C6H5 | 3-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3407 | CH | CH | CH | 5-Cl | C6H5 | 3-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3408 | CH | CH | CH | 5-Cl | C6H5 | 3-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3409 | CH | CH | CH | 5-Cl | C6H5 | 3-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3410 | CH | CH | CH | 5-Cl | C6H5 | 3-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3411 | CH | CH | CH | 5-Cl | C6H5 | 3-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3412 | CH | CH | CH | 5-Cl | C6H5 | 3-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3413 | CH | CH | CH | 5-Cl | C6H5 | 3-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3414 | CH | CH | CH | 5-Cl | C6H5 | 4-(CH3O)-C6H4 | CH3 | C(O) |
3415 | CH | CH | CH | 5-Cl | C6H5 | 4-(CH3O)-C6H4 | C2H5 | C(O) |
3416 | CH | CH | CH | 5-Cl | C6H5 | 4-(CH3O)-C6H4 | C6H5 | C(O) |
3417 | CH | CH | CH | 5-Cl | C6H5 | 4-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3418 | CH | CH | CH | 5-Cl | C6H5 | 4-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3419 | CH | CH | CH | 5-Cl | C6H5 | 4-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3420 | CH | CH | CH | 5-Cl | C6H5 | 4-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3421 | CH | CH | CH | 5-Cl | C6H5 | 4-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3422 | CH | CH | CH | 5-Cl | C6H5 | 4-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3423 | CH | CH | CH | 5-Cl | C6H5 | 4-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3424 | CH | CH | CH | 5-Cl | C6H5 | 4-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3425 | CH | CH | CH | 5-Cl | C6H5 | 2,3-(CH3O)2-C6H3 | CH3 | C(O) |
3426 | CH | CH | CH | 5-Cl | C6H5 | 2,3-(CH3O)2-C6H3 | C2H5 | C(O) |
3427 | CH | CH | CH | 5-Cl | C6H5 | 2,3-(CH3O)2-C6H3 | C6H5 | C(O) |
3428 | CH | CH | CH | 5-Cl | C6H5 | 2,3-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3429 | CH | CH | CH | 5-Cl | C6H5 | 2,3-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3430 | CH | CH | CH | 5-Cl | C6H5 | 2,3-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3431 | CH | CH | CH | 5-Cl | C6H5 | 2,3-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3432 | CH | CH | CH | 5-Cl | C6H5 | 2,3-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3433 | CH | CH | CH | 5-Cl | C6H5 | 2,3-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3434 | CH | CH | CH | 5-Cl | C6H5 | 2,3-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3435 | CH | CH | CH | 5-Cl | C6H5 | 2,3-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3436 | CH | CH | CH | 5-Cl | C6H5 | 2,4-(CH3O)2-C6H3 | CH3 | C(O) |
3437 | CH | CH | CH | 5-Cl | C6H5 | 2,4-(CH3O)2-C6H3 | C2H5 | C(O) |
3438 | CH | CH | CH | 5-Cl | C6H5 | 2,4-(CH3O)2-C6H3 | C6H5 | C(O) |
3439 | CH | CH | CH | 5-Cl | C6H5 | 2,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3440 | CH | CH | CH | 5-Cl | C6H5 | 2,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3441 | CH | CH | CH | 5-Cl | C6H5 | 2,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3442 | CH | CH | CH | 5-Cl | C6H5 | 2,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3443 | CH | CH | CH | 5-Cl | C6H5 | 2,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3444 | CH | CH | CH | 5-Cl | C6H5 | 2,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3445 | CH | CH | CH | 5-Cl | C6H5 | 2,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3446 | CH | CH | CH | 5-Cl | C6H5 | 2,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3447 | CH | CH | CH | 5-Cl | C6H5 | 3,4-(CH3O)2-C6H3 | CH3 | C(O) |
3448 | CH | CH | CH | 5-Cl | C6H5 | 3,4-(CH3O)2-C6H3 | C2H5 | C(O) |
3449 | CH | CH | CH | 5-Cl | C6H5 | 3,4-(CH3O)2-C6H3 | C6H5 | C(O) |
3450 | CH | CH | CH | 5-Cl | C6H5 | 3,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3451 | CH | CH | CH | 5-Cl | C6H5 | 3,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3452 | CH | CH | CH | 5-Cl | C6H5 | 3,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3453 | CH | CH | CH | 5-Cl | C6H5 | 3,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3454 | CH | CH | CH | 5-Cl | C6H5 | 3,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3455 | CH | CH | CH | 5-Cl | C6H5 | 3,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3456 | CH | CH | CH | 5-Cl | C6H5 | 3,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3457 | CH | CH | CH | 5-Cl | C6H5 | 3,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3458 | CH | CH | CH | 5-Cl | C6H5 | 3,5-(CH3O)2-C6H3 | CH3 | C(O) |
3459 | CH | CH | CH | 5-Cl | C6H5 | 3,5-(CH3O)2-C6H3 | C2H5 | C(O) |
3460 | CH | CH | CH | 5-Cl | C6H5 | 3,5-(CH3O)2-C6H3 | C6H5 | C(O) |
3461 | CH | CH | CH | 5-Cl | C6H5 | 3,5-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3462 | CH | CH | CH | 5-Cl | C6H5 | 3,5-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3463 | CH | CH | CH | 5-Cl | C6H5 | 3,5-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3464 | CH | CH | CH | 5-Cl | C6H5 | 3,5-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3465 | CH | CH | CH | 5-Cl | C6H5 | 3,5-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3466 | CH | CH | CH | 5-Cl | C6H5 | 3,5-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3467 | CH | CH | CH | 5-Cl | C6H5 | 3,5-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3468 | CH | CH | CH | 5-Cl | C6H5 | 3,5-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3469 | CH | CH | CH | 5-Cl | C6H5 | 3,4,5-(CH3O)3-C6H2 | CH3 | C(O) |
3470 | CH | CH | CH | 5-Cl | C6H5 | 3,4,5-(CH3O)3-C6H2 | C2H5 | C(O) |
3471 | CH | CH | CH | 5-Cl | C6H5 | 3,4,5-(CH3O)3-C6H2 | C6H5 | C(O) |
3472 | CH | CH | CH | 5-Cl | C6H5 | 3,4,5-(CH3O)3-C6H2 | 2-(CH3O)-C6H4 | C(O) |
3473 | CH | CH | CH | 5-Cl | C6H5 | 3,4,5-(CH3O)3-C6H2 | 3-(CH3O)-C6H4 | C(O) |
3474 | CH | CH | CH | 5-Cl | C6H5 | 3,4,5-(CH3O)3-C6H2 | 4-(CH3O)-C6H4 | C(O) |
3475 | CH | CH | CH | 5-Cl | C6H5 | 3,4,5-(CH3O)3-C6H2 | 2,3-(CH3O)2-C6H3 | C(O) |
3476 | CH | CH | CH | 5-Cl | C6H5 | 3,4,5-(CH3O)3-C6H2 | 2,4-(CH3O)2-C6H3 | C(O) |
3477 | CH | CH | CH | 5-Cl | C6H5 | 3,4,5-(CH3O)3-C6H2 | 3,4-(CH3O)2-C6H3 | C(O) |
3478 | CH | CH | CH | 5-Cl | C6H5 | 3,4,5-(CH3O)3-C6H2 | 3,5-(CH3O)2-C6H3 | C(O) |
3479 | CH | CH | CH | 5-Cl | C6H5 | 3,4,5-(CH3O)3-C6H2 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3480 | N | CH | CH | H | H | CH3 | CH3 | C(O) |
3481 | N | CH | CH | H | H | CH3 | C2H5 | C(O) |
3482 | N | CH | CH | H | H | CH3 | C6H5 | C(O) |
3483 | N | CH | CH | H | H | CH3 | 2-(CH3O)-C6H4 | C(O) |
3484 | N | CH | CH | H | H | CH3 | 3-(CH3O)-C6H4 | C(O) |
3485 | N | CH | CH | H | H | CH3 | 4-(CH3O)-C6H4 | C(O) |
3486 | N | CH | CH | H | H | CH3 | 2,3-(CH3O)2-C6H3 | C(O) |
3487 | N | CH | CH | H | H | CH3 | 2,4-(CH3O)2-C6H3 | C(O) |
3488 | N | CH | CH | H | H | CH3 | 3,4-(CH3O)2-C6H3 | C(O) |
3489 | N | CH | CH | H | H | CH3 | 3,5-(CH3O)2-C6H3 | C(O) |
3490 | N | CH | CH | H | H | CH3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3491 | N | CH | CH | H | H | C2H5 | CH3 | C(O) |
3492 | N | CH | CH | H | H | C2H5 | C2H5 | C(O) |
3493 | N | CH | CH | H | H | C2H5 | C6H5 | C(O) |
3494 | N | CH | CH | H | H | C2H5 | 2-(CH3O)-C6H4 | C(O) |
3495 | N | CH | CH | H | H | C2H5 | 3-(CH3O)-C6H4 | C(O) |
3496 | N | CH | CH | H | H | C2H5 | 4-(CH3O)-C6H4 | C(O) |
3497 | N | CH | CH | H | H | C2H5 | 2,3-(CH3O)2-C6H3 | C(O) |
3498 | N | CH | CH | H | H | C2H5 | 2,4-(CH3O)2-C6H3 | C(O) |
3499 | N | CH | CH | H | H | C2H5 | 3,4-(CH3O)2-C6H3 | C(O) |
3500 | N | CH | CH | H | H | C2H5 | 3,5-(CH3O)2-C6H3 | C(O) |
3501 | N | CH | CH | H | H | C2H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3502 | N | CH | CH | H | H | C6H5 | CH3 | C(O) |
3503 | N | CH | CH | H | H | C6H5 | C2H5 | C(O) |
3504 | N | CH | CH | H | H | C6H5 | C6H5 | C(O) |
3505 | N | CH | CH | H | H | C6H5 | 2-(CH3O)-C6H4 | C(O) |
3506 | N | CH | CH | H | H | C6H5 | 3-(CH3O)-C6H4 | C(O) |
3507 | N | CH | CH | H | H | C6H5 | 4-(CH3O)-C6H4 | C(O) |
3508 | N | CH | CH | H | H | C6H5 | 2,3-(CH3O)2-C6H3 | C(O) |
3509 | N | CH | CH | H | H | C6H5 | 2,4-(CH3O)2-C6H3 | C(O) |
3510 | N | CH | CH | H | H | C6H5 | 3,4-(CH3O)2-C6H3 | C(O) |
3511 | N | CH | CH | H | H | C6H5 | 3,5-(CH3O)2-C6H3 | C(O) |
3512 | N | CH | CH | H | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3513 | N | CH | CH | H | H | 2-(CH3O)-C6H4 | CH3 | C(O) |
3514 | N | CH | CH | H | H | 2-(CH3O)-C6H4 | C2H5 | C(O) |
3515 | N | CH | CH | H | H | 2-(CH3O)-C6H4 | C6H5 | C(O) |
3516 | N | CH | CH | H | H | 2-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3517 | N | CH | CH | H | H | 2-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3518 | N | CH | CH | H | H | 2-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3519 | N | CH | CH | H | H | 2-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3520 | N | CH | CH | H | H | 2-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3521 | N | CH | CH | H | H | 2-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3522 | N | CH | CH | H | H | 2-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3523 | N | CH | CH | H | H | 2-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3524 | N | CH | CH | H | H | 3-(CH3O)-C6H4 | CH3 | C(O) |
3525 | N | CH | CH | H | H | 3-(CH3O)-C6H4 | C2H5 | C(O) |
3526 | N | CH | CH | H | H | 3-(CH3O)-C6H4 | C6H5 | C(O) |
3527 | N | CH | CH | H | H | 3-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3528 | N | CH | CH | H | H | 3-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3529 | N | CH | CH | H | H | 3-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3530 | N | CH | CH | H | H | 3-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3531 | N | CH | CH | H | H | 3-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3532 | N | CH | CH | H | H | 3-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3533 | N | CH | CH | H | H | 3-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3534 | N | CH | CH | H | H | 3-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3535 | N | CH | CH | H | H | 4-(CH3O)-C6H4 | CH3 | C(O) |
3536 | N | CH | CH | H | H | 4-(CH3O)-C6H4 | C2H5 | C(O) |
3537 | N | CH | CH | H | H | 4-(CH3O)-C6H4 | C6H5 | C(O) |
3538 | N | CH | CH | H | H | 4-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3539 | N | CH | CH | H | H | 4-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3540 | N | CH | CH | H | H | 4-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3541 | N | CH | CH | H | H | 4-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3542 | N | CH | CH | H | H | 4-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3543 | N | CH | CH | H | H | 4-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3544 | N | CH | CH | H | H | 4-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3545 | N | CH | CH | H | H | 4-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3546 | N | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | CH3 | C(O) |
3547 | N | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | C2H5 | C(O) |
3548 | N | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | C6H5 | C(O) |
3549 | N | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3550 | N | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3551 | N | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3552 | N | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3553 | N | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3554 | N | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3555 | N | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3556 | N | CH | CH | H | H | 2,3-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3557 | N | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | CH3 | C(O) |
3558 | N | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | C2H5 | C(O) |
3559 | N | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | C6H5 | C(O) |
3560 | N | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3561 | N | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3562 | N | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3563 | N | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3564 | N | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3565 | N | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3566 | N | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3567 | N | CH | CH | H | H | 2,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3568 | N | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | CH3 | C(O) |
3569 | N | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | C2H5 | C(O) |
3570 | N | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | C6H5 | C(O) |
3571 | N | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3572 | N | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3573 | N | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3574 | N | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3575 | N | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3576 | N | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3577 | N | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3578 | N | CH | CH | H | H | 3,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3579 | N | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | CH3 | C(O) |
3580 | N | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | C2H5 | C(O) |
3581 | N | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | C6H5 | C(O) |
3582 | N | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3583 | N | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3584 | N | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3585 | N | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3586 | N | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3587 | N | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3588 | N | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3589 | N | CH | CH | H | H | 3,5-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3590 | N | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | CH3 | C(O) |
3591 | N | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | C2H5 | C(O) |
3592 | N | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | C6H5 | C(O) |
3593 | N | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 2-(CH3O)-C6H4 | C(O) |
3594 | N | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 3-(CH3O)-C6H4 | C(O) |
3595 | N | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 4-(CH3O)-C6H4 | C(O) |
3596 | N | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 2,3-(CH3O)2-C6H3 | C(O) |
3597 | N | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 2,4-(CH3O)2-C6H3 | C(O) |
3598 | N | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 3,4-(CH3O)2-C6H3 | C(O) |
3599 | N | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 3,5-(CH3O)2-C6H3 | C(O) |
3600 | N | CH | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3601 | CH | N | CH | H | H | CH3 | CH3 | C(O) |
3602 | CH | N | CH | H | H | CH3 | C2H5 | C(O) |
3603 | CH | N | CH | H | H | CH3 | C6H5 | C(O) |
3604 | CH | N | CH | H | H | CH3 | 2-(CH3O)-C6H4 | C(O) |
3605 | CH | N | CH | H | H | CH3 | 3-(CH3O)-C6H4 | C(O) |
3606 | CH | N | CH | H | H | CH3 | 4-(CH3O)-C6H4 | C(O) |
3607 | CH | N | CH | H | H | CH3 | 2,3-(CH3O)2-C6H3 | C(O) |
3608 | CH | N | CH | H | H | CH3 | 2,4-(CH3O)2-C6H3 | C(O) |
3609 | CH | N | CH | H | H | CH3 | 3,4-(CH3O)2-C6H3 | C(O) |
3610 | CH | N | CH | H | H | CH3 | 3,5-(CH3O)2-C6H3 | C(O) |
3611 | CH | N | CH | H | H | CH3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3612 | CH | N | CH | H | H | C2H5 | CH3 | C(O) |
3613 | CH | N | CH | H | H | C2H5 | C2H5 | C(O) |
3614 | CH | N | CH | H | H | C2H5 | C6H5 | C(O) |
3615 | CH | N | CH | H | H | C2H5 | 2-(CH3O)-C6H4 | C(O) |
3616 | CH | N | CH | H | H | C2H5 | 3-(CH3O)-C6H4 | C(O) |
3617 | CH | N | CH | H | H | C2H5 | 4-(CH3O)-C6H4 | C(O) |
3618 | CH | N | CH | H | H | C2H5 | 2,3-(CH3O)2-C6H3 | C(O) |
3619 | CH | N | CH | H | H | C2H5 | 2,4-(CH3O)2-C6H3 | C(O) |
3620 | CH | N | CH | H | H | C2H5 | 3,4-(CH3O)2-C6H3 | C(O) |
3621 | CH | N | CH | H | H | C2H5 | 3,5-(CH3O)2-C6H3 | C(O) |
3622 | CH | N | CH | H | H | C2H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3623 | CH | N | CH | H | H | C6H5 | CH3 | C(O) |
3624 | CH | N | CH | H | H | C6H5 | C2H5 | C(O) |
3625 | CH | N | CH | H | H | C6H5 | C6H5 | C(O) |
3626 | CH | N | CH | H | H | C6H5 | 2-(CH3O)-C6H4 | C(O) |
3636 | CH | N | CH | H | H | C6H5 | 3-(CH3O)-C6H4 | C(O) |
3628 | CH | N | CH | H | H | C6H5 | 4-(CH3O)-C6H4 | C(O) |
3629 | CH | N | CH | H | H | C6H5 | 2,3-(CH3O)2-C6H3 | C(O) |
3630 | CH | N | CH | H | H | C6H5 | 2,4-(CH3O)2-C6H3 | C(O) |
3631 | CH | N | CH | H | H | C6H5 | 3,4-(CH3O)2-C6H3 | C(O) |
3632 | CH | N | CH | H | H | C6H5 | 3,5-(CH3O)2-C6H3 | C(O) |
3633 | CH | N | CH | H | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3634 | CH | N | CH | H | H | 2-(CH3O)-C6H4 | CH3 | C(O) |
3635 | CH | N | CH | H | H | 2-(CH3O)-C6H4 | C2H5 | C(O) |
3636 | CH | N | CH | H | H | 2-(CH3O)-C6H4 | C6H5 | C(O) |
3637 | CH | N | CH | H | H | 2-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3638 | CH | N | CH | H | H | 2-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3639 | CH | N | CH | H | H | 2-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3640 | CH | N | CH | H | H | 2-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3641 | CH | N | CH | H | H | 2-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3642 | CH | N | CH | H | H | 2-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3643 | CH | N | CH | H | H | 2-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3644 | CH | N | CH | H | H | 2-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3645 | CH | N | CH | H | H | 3-(CH3O)-C6H4 | CH3 | C(O) |
3646 | CH | N | CH | H | H | 3-(CH3O)-C6H4 | C2H5 | C(O) |
3647 | CH | N | CH | H | H | 3-(CH3O)-C6H4 | C6H5 | C(O) |
3648 | CH | N | CH | H | H | 3-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3649 | CH | N | CH | H | H | 3-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3650 | CH | N | CH | H | H | 3-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3651 | CH | N | CH | H | H | 3-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3652 | CH | N | CH | H | H | 3-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3653 | CH | N | CH | H | H | 3-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3654 | CH | N | CH | H | H | 3-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3655 | CH | N | CH | H | H | 3-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3656 | CH | N | CH | H | H | 4-(CH3O)-C6H4 | CH3 | C(O) |
3657 | CH | N | CH | H | H | 4-(CH3O)-C6H4 | C2H5 | C(O) |
3658 | CH | N | CH | H | H | 4-(CH3O)-C6H4 | C6H5 | C(O) |
3659 | CH | N | CH | H | H | 4-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3660 | CH | N | CH | H | H | 4-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3661 | CH | N | CH | H | H | 4-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3662 | CH | N | CH | H | H | 4-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3663 | CH | N | CH | H | H | 4-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3664 | CH | N | CH | H | H | 4-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3665 | CH | N | CH | H | H | 4-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3666 | CH | N | CH | H | H | 4-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3667 | CH | N | CH | H | H | 2,3-(CH3O)2-C6H3 | CH3 | C(O) |
3668 | CH | N | CH | H | H | 2,3-(CH3O)2-C6H3 | C2H5 | C(O) |
3669 | CH | N | CH | H | H | 2,3-(CH3O)2-C6H3 | C6H5 | C(O) |
3670 | CH | N | CH | H | H | 2,3-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3671 | CH | N | CH | H | H | 2,3-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3672 | CH | N | CH | H | H | 2,3-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3673 | CH | N | CH | H | H | 2,3-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3674 | CH | N | CH | H | H | 2,3-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3675 | CH | N | CH | H | H | 2,3-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3676 | CH | N | CH | H | H | 2,3-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3677 | CH | N | CH | H | H | 2,3-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3678 | CH | N | CH | H | H | 2,4-(CH3O)2-C6H3 | CH3 | C(O) |
3679 | CH | N | CH | H | H | 2,4-(CH3O)2-C6H3 | C2H5 | C(O) |
3680 | CH | N | CH | H | H | 2,4-(CH3O)2-C6H3 | C6H5 | C(O) |
3681 | CH | N | CH | H | H | 2,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3682 | CH | N | CH | H | H | 2,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3683 | CH | N | CH | H | H | 2,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3684 | CH | N | CH | H | H | 2,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3685 | CH | N | CH | H | H | 2,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3686 | CH | N | CH | H | H | 2,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3687 | CH | N | CH | H | H | 2,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3688 | CH | N | CH | H | H | 2,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3689 | CH | N | CH | H | H | 3,4-(CH3O)2-C6H3 | CH3 | C(O) |
3690 | CH | N | CH | H | H | 3,4-(CH3O)2-C6H3 | C2H5 | C(O) |
3691 | CH | N | CH | H | H | 3,4-(CH3O)2-C6H3 | C6H5 | C(O) |
3692 | CH | N | CH | H | H | 3,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3693 | CH | N | CH | H | H | 3,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3694 | CH | N | CH | H | H | 3,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3695 | CH | N | CH | H | H | 3,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3696 | CH | N | CH | H | H | 3,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3697 | CH | N | CH | H | H | 3,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3698 | CH | N | CH | H | H | 3,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3699 | CH | N | CH | H | H | 3,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3700 | CH | N | CH | H | H | 3,5-(CH3O)2-C6H3 | CH3 | C(O) |
3701 | CH | N | CH | H | H | 3,5-(CH3O)2-C6H3 | C2H5 | C(O) |
3702 | CH | N | CH | H | H | 3,5-(CH3O)2-C6H3 | C6H5 | C(O) |
3703 | CH | N | CH | H | H | 3,5-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3704 | CH | N | CH | H | H | 3,5-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3705 | CH | N | CH | H | H | 3,5-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3706 | CH | N | CH | H | H | 3,5-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3707 | CH | N | CH | H | H | 3,5-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3708 | CH | N | CH | H | H | 3,5-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3709 | CH | N | CH | H | H | 3,5-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3710 | CH | N | CH | H | H | 3,5-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3711 | CH | N | CH | H | H | 3,4,5-(CH3O)3-C6H2 | CH3 | C(O) |
3712 | CH | N | CH | H | H | 3,4,5-(CH3O)3-C6H2 | C2H5 | C(O) |
3713 | CH | N | CH | H | H | 3,4,5-(CH3O)3-C6H2 | C6H5 | C(O) |
3714 | CH | N | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 2-(CH3O)-C6H4 | C(O) |
3715 | CH | N | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 3-(CH3O)-C6H4 | C(O) |
3716 | CH | N | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 4-(CH3O)-C6H4 | C(O) |
3717 | CH | N | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 2,3-(CH3O)2-C6H3 | C(O) |
3718 | CH | N | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 2,4-(CH3O)2-C6H3 | C(O) |
3719 | CH | N | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 3,4-(CH3O)2-C6H3 | C(O) |
3720 | CH | N | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 3,5-(CH3O)2-C6H3 | C(O) |
3721 | CH | N | CH | H | H | 3,4,5-(CH3O)3-C6H2 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3722 | CH | CH | N | H | H | CH3 | CH3 | C(O) |
3723 | CH | CH | N | H | H | CH3 | C2H5 | C(O) |
3724 | CH | CH | N | H | H | CH3 | C6H5 | C(O) |
3725 | CH | CH | N | H | H | CH3 | 2-(CH3O)-C6H4 | C(O) |
3726 | CH | CH | N | H | H | CH3 | 3-(CH3O)-C6H4 | C(O) |
3727 | CH | CH | N | H | H | CH3 | 4-(CH3O)-C6H4 | C(O) |
3728 | CH | CH | N | H | H | CH3 | 2,3-(CH3O)2-C6H3 | C(O) |
3729 | CH | CH | N | H | H | CH3 | 2,4-(CH3O)2-C6H3 | C(O) |
3730 | CH | CH | N | H | H | CH3 | 3,4-(CH3O)2-C6H3 | C(O) |
3731 | CH | CH | N | H | H | CH3 | 3,5-(CH3O)2-C6H3 | C(O) |
3732 | CH | CH | N | H | H | CH3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3733 | CH | CH | N | H | H | C2H5 | CH3 | C(O) |
3734 | CH | CH | N | H | H | C2H5 | C2H5 | C(O) |
3735 | CH | CH | N | H | H | C2H5 | C6H5 | C(O) |
3736 | CH | CH | N | H | H | C2H5 | 2-(CH3O)-C6H4 | C(O) |
3737 | CH | CH | N | H | H | C2H5 | 3-(CH3O)-C6H4 | C(O) |
3738 | CH | CH | N | H | H | C2H5 | 4-(CH3O)-C6H4 | C(O) |
3739 | CH | CH | N | H | H | C2H5 | 2,3-(CH3O)2-C6H3 | C(O) |
3740 | CH | CH | N | H | H | C2H5 | 2,4-(CH3O)2-C6H3 | C(O) |
3741 | CH | CH | N | H | H | C2H5 | 3,4-(CH3O)2-C6H3 | C(O) |
3742 | CH | CH | N | H | H | C2H5 | 3,5-(CH3O)2-C6H3 | C(O) |
3743 | CH | CH | N | H | H | C2H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3744 | CH | CH | N | H | H | C6H5 | CH3 | C(O) |
3745 | CH | CH | N | H | H | C6H5 | C2H5 | C(O) |
3746 | CH | CH | N | H | H | C6H5 | C6H5 | C(O) |
3747 | CH | CH | N | H | H | C6H5 | 2-(CH3O)-C6H4 | C(O) |
3748 | CH | CH | N | H | H | C6H5 | 3-(CH3O)-C6H4 | C(O) |
3749 | CH | CH | N | H | H | C6H5 | 4-(CH3O)-C6H4 | C(O) |
3750 | CH | CH | N | H | H | C6H5 | 2,3-(CH3O)2-C6H3 | C(O) |
3751 | CH | CH | N | H | H | C6H5 | 2,4-(CH3O)2-C6H3 | C(O) |
3752 | CH | CH | N | H | H | C6H5 | 3,4-(CH3O)2-C6H3 | C(O) |
3753 | CH | CH | N | H | H | C6H5 | 3,5-(CH3O)2-C6H3 | C(O) |
3754 | CH | CH | N | H | H | C6H5 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3755 | CH | CH | N | H | H | 2-(CH3O)-C6H4 | CH3 | C(O) |
3756 | CH | CH | N | H | H | 2-(CH3O)-C6H4 | C2H5 | C(O) |
3757 | CH | CH | N | H | H | 2-(CH3O)-C6H4 | C6H5 | C(O) |
3758 | CH | CH | N | H | H | 2-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3759 | CH | CH | N | H | H | 2-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3760 | CH | CH | N | H | H | 2-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3761 | CH | CH | N | H | H | 2-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3762 | CH | CH | N | H | H | 2-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3763 | CH | CH | N | H | H | 2-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3764 | CH | CH | N | H | H | 2-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3765 | CH | CH | N | H | H | 2-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3766 | CH | CH | N | H | H | 3-(CH3O)-C6H4 | CH3 | C(O) |
3767 | CH | CH | N | H | H | 3-(CH3O)-C6H4 | C2H5 | C(O) |
3768 | CH | CH | N | H | H | 3-(CH3O)-C6H4 | C6H5 | C(O) |
3769 | CH | CH | N | H | H | 3-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3770 | CH | CH | N | H | H | 3-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3771 | CH | CH | N | H | H | 3-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3772 | CH | CH | N | H | H | 3-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3773 | CH | CH | N | H | H | 3-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3774 | CH | CH | N | H | H | 3-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3775 | CH | CH | N | H | H | 3-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3776 | CH | CH | N | H | H | 3-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3777 | CH | CH | N | H | H | 4-(CH3O)-C6H4 | CH3 | C(O) |
3778 | CH | CH | N | H | H | 4-(CH3O)-C6H4 | C2H5 | C(O) |
3779 | CH | CH | N | H | H | 4-(CH3O)-C6H4 | C6H5 | C(O) |
3780 | CH | CH | N | H | H | 4-(CH3O)-C6H4 | 2-(CH3O)-C6H4 | C(O) |
3781 | CH | CH | N | H | H | 4-(CH3O)-C6H4 | 3-(CH3O)-C6H4 | C(O) |
3782 | CH | CH | N | H | H | 4-(CH3O)-C6H4 | 4-(CH3O)-C6H4 | C(O) |
3783 | CH | CH | N | H | H | 4-(CH3O)-C6H4 | 2,3-(CH3O)2-C6H3 | C(O) |
3784 | CH | CH | N | H | H | 4-(CH3O)-C6H4 | 2,4-(CH3O)2-C6H3 | C(O) |
3785 | CH | CH | N | H | H | 4-(CH3O)-C6H4 | 3,4-(CH3O)2-C6H3 | C(O) |
3786 | CH | CH | N | H | H | 4-(CH3O)-C6H4 | 3,5-(CH3O)2-C6H3 | C(O) |
3787 | CH | CH | N | H | H | 4-(CH3O)-C6H4 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3788 | CH | CH | N | H | H | 2,3-(CH3O)2-C6H3 | CH3 | C(O) |
3789 | CH | CH | N | H | H | 2,3-(CH3O)2-C6H3 | C2H5 | C(O) |
3790 | CH | CH | N | H | H | 2,3-(CH3O)2-C6H3 | C6H5 | C(O) |
3791 | CH | CH | N | H | H | 2,3-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3792 | CH | CH | N | H | H | 2,3-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3793 | CH | CH | N | H | H | 2,3-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3794 | CH | CH | N | H | H | 2,3-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3795 | CH | CH | N | H | H | 2,3-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3796 | CH | CH | N | H | H | 2,3-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3797 | CH | CH | N | H | H | 2,3-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3798 | CH | CH | N | H | H | 2,3-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3799 | CH | CH | N | H | H | 2,4-(CH3O)2-C6H3 | CH3 | C(O) |
3800 | CH | CH | N | H | H | 2,4-(CH3O)2-C6H3 | C2H5 | C(O) |
3801 | CH | CH | N | H | H | 2,4-(CH3O)2-C6H3 | C6H5 | C(O) |
3802 | CH | CH | N | H | H | 2,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3803 | CH | CH | N | H | H | 2,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3804 | CH | CH | N | H | H | 2,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3805 | CH | CH | N | H | H | 2,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3806 | CH | CH | N | H | H | 2,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3807 | CH | CH | N | H | H | 2,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3808 | CH | CH | N | H | H | 2,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3809 | CH | CH | N | H | H | 2,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3810 | CH | CH | N | H | H | 3,4-(CH3O)2-C6H3 | CH3 | C(O) |
3811 | CH | CH | N | H | H | 3,4-(CH3O)2-C6H3 | C2H5 | C(O) |
3812 | CH | CH | N | H | H | 3,4-(CH3O)2-C6H3 | C6H5 | C(O) |
3813 | CH | CH | N | H | H | 3,4-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3814 | CH | CH | N | H | H | 3,4-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3815 | CH | CH | N | H | H | 3,4-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3816 | CH | CH | N | H | H | 3,4-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3817 | CH | CH | N | H | H | 3,4-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3818 | CH | CH | N | H | H | 3,4-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3819 | CH | CH | N | H | H | 3,4-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3820 | CH | CH | N | H | H | 3,4-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3821 | CH | CH | N | H | H | 3,5-(CH3O)2-C6H3 | CH3 | C(O) |
3822 | CH | CH | N | H | H | 3,5-(CH3O)2-C6H3 | C2H5 | C(O) |
3823 | CH | CH | N | H | H | 3,5-(CH3O)2-C6H3 | C6H5 | C(O) |
3824 | CH | CH | N | H | H | 3,5-(CH3O)2-C6H3 | 2-(CH3O)-C6H4 | C(O) |
3825 | CH | CH | N | H | H | 3,5-(CH3O)2-C6H3 | 3-(CH3O)-C6H4 | C(O) |
3826 | CH | CH | N | H | H | 3,5-(CH3O)2-C6H3 | 4-(CH3O)-C6H4 | C(O) |
3827 | CH | CH | N | H | H | 3,5-(CH3O)2-C6H3 | 2,3-(CH3O)2-C6H3 | C(O) |
3828 | CH | CH | N | H | H | 3,5-(CH3O)2-C6H3 | 2,4-(CH3O)2-C6H3 | C(O) |
3829 | CH | CH | N | H | H | 3,5-(CH3O)2-C6H3 | 3,4-(CH3O)2-C6H3 | C(O) |
3830 | CH | CH | N | H | H | 3,5-(CH3O)2-C6H3 | 3,5-(CH3O)2-C6H3 | C(O) |
3831 | CH | CH | N | H | H | 3,5-(CH3O)2-C6H3 | 3,4,5-(CH3O)3-C6H2 | C(O) |
3832 | CH | CH | N | H | H | 3,4,5-(CH3O)3-C6H2 | CH3 | C(O) |
3833 | CH | CH | N | H | H | 3,4,5-(CH3O)3-C6H2 | C2H5 | C(O) |
3834 | CH | CH | N | H | H | 3,4,5-(CH3O)3-C6H2 | C6H5 | C(O) |
3835 | CH | CH | N | H | H | 3,4,5-(CH3O)3-C6H2 | 2-(CH3O)-C6H4 | C(O) |
3836 | CH | CH | N | H | H | 3,4,5-(CH3O)3-C6H2 | 3-(CH3O)-C6H4 | C(O) |
3837 | CH | CH | N | H | H | 3,4,5-(CH3O)3-C6H2 | 4-(CH3O)-C6H4 | C(O) |
3838 | CH | CH | N | H | H | 3,4,5-(CH3O)3-C6H2 | 2,3-(CH3O)2-C6H3 | C(O) |
3839 | CH | CH | N | H | H | 3,4,5-(CH3O)3-C6H2 | 2,4-(CH3O)2-C6H3 | C(O) |
3840 | CH | CH | N | H | H | 3,4,5-(CH3O)3-C6H2 | 3,4-(CH3O)2-C6H3 | C(O) |
3841 | CH | CH | N | H | H | 3,4,5-(CH3O)3-C6H2 | 3,5-(CH3O)2-C6H3 | C(O) |
3842 | CH | CH | N | H | H | 3,4,5-(CH3O)3-C6H2 | 3,4,5-(CH3O)3-C6H2 | C(O) |
类似地,按照一般工艺F,还有可能制备根据本发明的下列化合物(实施例3843至6260):
实施例3843-5051:
A、C、D、R、R1、R6、R8和X具有如上实施例2635至3842所给出的含义,Y在每种情况下都是S(O);
实施例5052-6260:
A、C、D、R、R1、R6、R8和X具有如上实施例2635至3842所给出的含义,Y在每种情况下都是SO2。
药理试验结果
在所选择的肿瘤模型中所进行的体外试验显示下列药理活性。
实施例1:抗增殖性质
使用既定的肿瘤细胞系,在增殖测定法中检查物质D-70260、D-70744、D-80815、D-80816和D-80819(实施例C2.3、D4、F2、F3和F4)的抗增殖活性(Scudiero et al.,Cancer Res.,48:4827-33,1987)。所用试验测定了线粒体脱氢酶活性,允许细胞存活,间接测定细胞数。所用细胞系是人细胞系HeLa/KB(CCL17)、SK-OV-3(HTB77)、MCF-7(HTB22)和鼠白血病细胞系L1210(CCL219)。它们已被鉴别得非常充分,从ATCC获得既定的细胞系,培养之。
表1所总结的结果显示,物质D-70260、D-70744和D-80816(实施例C2.3、D4和F3)具有非常有力的抗增殖作用。相反,结构上相关的化合物D-80815和D-80819(实施例F2和F4)显示没有显著的作用。因此,存在明确的结构-活性关系。
表1:不同衍生物在XTT细胞毒性试验中对细胞系HeLa/KB、SK-OV-3、MCF-7和L1210的抗增殖活性。所要说明的是抑制作用以在3.16μg/ml浓度下的百分比表示。
图1:D-80816(实施例F3)在XTT细胞毒性试验中对细胞系HeLa/KB、SK-OV-3、MCF-7和L1210的浓度依赖性抗增殖活性图示(A)。
D-80816
实施例2:D-80816(实施例F3)在体内中空纤维模型中的效果
为了测定在动物模型(裸鼠)中的可利用性和功效,在i.p.或s.c.植入的中空纤维中培养细胞系HeLa/KB、MCF-7和L1210(Hollingshead el al.,Life Sciences 57,131-41,1995)。将供试物质D-80816给药四次,剂量为100mg/kg i.p.。在第5天治疗结束后,移植出纤维,利用XTT测定法测定所得肿瘤细胞的细胞活力。D-80816对所有细胞系和植入部位显示最大100%抑制,一般毒性LD50>1000mg/kg(i.p.)。
表2:D-80816在中空纤维试验中对肿瘤细胞系HeLa/KB、MCF-7和L1210的体内活性(剂量:4×100mg/kg i.p.)
实施例3:D-80816在RKOp27模型中的细胞周期特异性作用
使用RKOp27细胞系统(M.Schmidt et al.,Oncogene 19(20):2423-9,2000)作为模型,检查细胞周期特异性作用。RKO是人结肠癌系,其中蜕皮素表达系统诱导表达细胞周期抑制剂p27Kip1,导致细胞周期特异性地停止于G1(图2)。具有非特异性作用的物质抑制增殖,与RKO细胞是否停止于G1无关。相反,细胞周期特异性物质、例如微管蛋白抑制剂,仅在细胞没有停止和正在经历细胞周期时有细胞毒性。这里,D-80816显示细胞周期特异性作用,也就是说,仅在没有停止于细胞周期G1的未被诱导细胞中才能测量到浓度依赖性抗增殖作用(图3)。因此,不得不假设D-80816和衍生物作用为某种明确的分子机理。
图2:诱导p27/kip1表达引起细胞周期停止于G1的图示和细胞+/-诱导剂(muristerone A)与供试物质的处理顺序的图示
图3:D-80816(实施例F3)对停止于细胞周期G1期(被诱导的)或正在经历细胞周期、即指数增殖的RKO结肠癌细胞的抗增殖效果
所用方法的说明
细胞脱氧酶活性的XTT试验
在37℃、5%CO2和95%大气湿度下,在熏蒸恒温箱中,在标准条件下培养粘附生长的肿瘤细胞系HeLa/KB、SK-OV-3、MCF-7、L1210。在实验的第1天,使用胰蛋白酶/EDTA剥离细胞,离心沉淀。随后,将细胞沉淀按适当的细胞数重新悬浮在各自的培养基中,在96孔微量滴定板中反应。然后将平板在熏蒸恒温箱中培养过夜。制备供试物质在DMSO中的10mM储备溶液,在实验的第2天用培养基稀释至适当的浓度。然后向细胞加入含有物质的培养基,在熏蒸恒温箱中培育45小时。作为对照,使用没有用供试物质处理的细胞。就XTT测定法而言,将1mg/ml XTT(3’-[1-(苯氨基羰基)-3,4-四唑鎓]双(4-甲氧基-6-硝基)苯磺酸钠)溶于不含酚红的RPMI-1640培养基中。另外,制备0.383mg/ml PMS(N-甲基二苯并吡嗪甲基硫酸盐)在磷酸缓冲盐水溶液(PBS)中的溶液。在实验的第4天,向细胞平板上移加75μl/孔XTT-PMS混合物,在此期间与供试物质培育45小时。为此,在使用前将XTT溶液与PMS溶液按50∶1(v∶v)混合。然后将细胞平板在熏蒸恒温箱中培育另外3小时,在光度计中测定光密度(OD490nm)。
借助所测定的OD490nm,相对于对照计算抑制百分比,以半对数方式绘制浓度-活性曲线。利用Graphpad程序从浓度-活性曲线借助回归分析计算IC50。
体内中空纤维模型中抗增殖活性的测定
向由聚(亚乙烯基)氟制成的中空纤维引入肿瘤细胞系HeLa/KB、MCF-7和L1210(5×106细胞/ml),移植到裸鼠的生理体腔内(腹膜内i.p.或皮下s.c.)。在每只供试动物中,总共移植6支中空纤维(3i.p.,3s.c.),其中含有有关的肿瘤细胞系。将一组6只动物用供试物质处理(每日1次i.p.,共计4天)(可以?)。仅用溶剂纤基乙酸钠处理的动物充当对照组。最后一次施用物质后一天,移植出中空纤维。利用XTT测定法测定每支中空纤维中有代谢活性、有活力的细胞数(见上)。由此测定供试物质的抗肿瘤活性,以相对于对照的抑制%表示。
利用RKOp27模型的细胞周期分析
该测定法在96孔平板中进行。可诱导的p27kip1表达使细胞的生长完全停止,但是细胞没有死亡。通过比较对被诱导和未被诱导的细胞的功效,有可能得出关于治疗剂作用机理(细胞周期特异性)的结论。接种未被诱导的细胞,与未被诱导的细胞相比细胞数高约四倍,因为在测定期间不再分化(被诱导的细胞为2×104个/孔,未被诱导的细胞为0.6×104个/孔)。对照是未被处理的细胞(+/-诱导)。诱导是用3μM muristerone A进行的。第1天,接种细胞(+/-muristeroneA),在37℃下培育24小时。第2天,加入供试物质(对照为DMSO),将样本在37℃下培育另外48小时,然后进行标准XTT测定(见上)。
根据本发明的化合物能够用作药物治疗哺乳动物、特别是人类的疾病、特别是肿瘤疾病。
可以口服、局部或肠胃外方式(i.m.,i.v.,s.c.)以适合的给药剂型给药。
可以提到的适合的给药剂型的实例有:
实施例I
包含50mg活性化合物的片剂
组成:
(1)活性化合物 50.0mg
(2)乳糖 98.0mg
(3)玉米淀粉 50.0mg
(4)聚乙烯吡咯烷酮 15.0mg
(5)硬脂酸镁 2.0mg
总计: 215.0mg
制备:
将(1)、(2)和(3)混合,使用(4)的水溶液造粒。将(5)与干燥的颗粒混合。将该混合物压制成片。
实施例II
包含50mg活性化合物的胶囊剂
组成:
(1)活性化合物 50.0mg
(2)干燥的玉米淀粉 58.0mg
(3)粉末状的乳糖 50.0mg
(4)硬脂酸镁 2.0mg
总计: 160.0mg
制备:
将(1)与(3)研磨。在剧烈混合的同时,将该混合物加入到(2)与(4)的混合物中。在胶囊填充机中,将该粉末混合物填充在3号硬明胶胶囊中。
Claims (7)
1、式I化合物或其互变异构体、立体异构体、混合物或药学上可接受的盐
其中
R1是氢、(C6-C14)-芳基—未取代的或者被相同或不同的取代基完全或部分取代、(C1-C13)-杂芳基—含有至少一个至四个N、NH、O和/或S作为环成员并且是未取代的或者被相同或不同的取代基完全或部分取代、(C3-C8)-环烷基—未取代的或者被相同或不同的取代基完全或部分取代、或者直链或支链(C1-C20)-烷基—未取代的或者被相同或不同的取代基完全或部分取代;
A、B、C或D彼此独立为被R2-R5取代的氮原子或碳原子;
R2、R3、R4和R5彼此独立为游离电子对(如果键合伴侣A、B、C或D是氮原子)、氢、卤素、氰基、硝基、羟基、直链或支链(C1-C6)-烷基、被一个或多个卤原子取代的直链或支链(C1-C6)-烷基、直链或支链(C1-C6)-烷氧基、被一个或多个卤原子取代的直链或支链(C1-C6)-烷氧基、直链或支链(C1-C6)-亚烷二氧基、(C1-C6)-烷基羰基氧基、(C1-C6)-烷氧基羰基氧基、(C1-C6)-烷硫基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、羧基、(C1-C6)-烷基羧酸酯、酰胺、N-(C1-C6)-烷基酰胺、N,N-二-(C1-C6)-烷基酰胺、(C1-C6)-烷氧基-(C1-C6)-烷基、氨基、单-(C1-C6)-烷基氨基、二-(C1-C6)-烷基氨基—其中两个(C1-C6)基团一起可以构成可选含有一个或多个NH、N-(C1-C6)-烷基、O或S的环、(C6-C14)-芳基、(C6-C14)-芳氧基、(C6-C14)-芳基-(C1-C6)-烷基、(C6-C14)-芳基-(C1-C6)-烷氧基-(C1-C6)-烷基、(C1-C6)-烷基羰基、(C1-C6)-烷氧基羰基、羟基,其中两个直接相邻的基团可以彼此连接;
R6是(C6-C14)-芳基—未取代的或者被相同或不同的取代基完全或部分取代、(C1-C13)-杂芳基—有至少一个至四个N、NH、O和/或S作为环成员并且是未取代的或者被相同或不同的取代基完全或部分取代、(C3-C8)-环烷基—未取代的或者被相同或不同的取代基完全或部分取代、直链或支链(C1-C20)-烷基—未取代的或者被相同或不同的取代基完全或部分取代,其中相同或不同的取代基选自氢、氟、氯、溴、碘、氰基、硝基、羟基、(C1-C6)-烷基、(C1-C6)-烷氧基、羧基、被一个或多个相同或不同的卤原子取代的(C1-C6)-烷基、被一个或多个相同或不同的卤原子取代的(C1-C6)-烷氧基、直链或支链(C2-C6)-烯基、直链或支链(C2-C6)-炔基、(C3-C8)-环烷基、直链或支链(C1-C6)-烷氧基、直链或支链(C1-C6)-亚烷二氧基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C6-C14)-芳基、(C6-C14)-芳基-(C1-C6)-烷基、(C6-C14)-芳基-(C1-C4)-烷氧基-(C1-C6)-烷基;
X是羰基(C=O)、亚砜(S=O)或磺酰基(SO2);
Y是氧原子或被基团R7取代的氮原子(NR7),其中
R7是(C6-C14)-芳基—未取代的或者被相同或不同的取代基完全或部分取代、(C1-C13)-杂芳基—含有至少一个至四个N、NH、O和/或S作为环成员并且是未取代的或者被相同或不同的取代基完全或部分取代、(C3-C8)-环烷基—未取代的或者被相同或不同的取代基完全或部分取代、直链或支链(C1-C20)-烷基—未取代的或者被相同或不同的取代基完全或部分取代,其中相同或不同的取代基选自氢、氟、氯、溴、碘、氰基、硝基、羟基、(C1-C6)-烷基、(C1-C6)-烷氧基、羧基、被一个或多个相同或不同的卤原子取代的(C1-C6)-烷基、被一个或多个相同或不同的卤原子取代的(C1-C6)-烷氧基、直链或支链(C2-C6)-烯基、直链或支链(C2-C6)-炔基、(C3-C8)-环烷基、直链或支链(C1-C6)-烷氧基、直链或支链(C1-C6)-亚烷二氧基、(C1-C6)-烷氧基-(C1-C6)-烷基、直链或支链单-(C1-C6)-烷基氨基、直链或支链二-(C1-C6)-烷基氨基—其中两个(C1-C4)基团一起可以构成可选含有一个或多个NH、N-(C1-C6)-烷基、O或S的环、(C6-C14)-芳基、(C6-C14)-芳基-(C1-C6)-烷基、(C6-C14)-芳基-(C1-C4)-烷氧基-(C1-C6)-烷基、(C1-C6)-烷基羰基、(C1-C6)-烷氧基羰基;
n是0或1,其条件是如果n=0,那么
Z是被基团R8取代的碳原子(C-R8),其中
R8是(C6-C14)-芳基—未取代的或者被相同或不同的取代基完全或部分取代、(C1-C13)-杂芳基—含有至少一个至四个N、NH、O和/或S作为环成员并且是未取代的或者被相同或不同的取代基完全或部分取代、(C3-C8)-环烷基—未取代的或者被相同或不同的取代基完全或部分取代、直链或支链(C1-C20)-烷基—未取代的或者被相同或不同的取代基完全或部分取代,其中相同或不同的取代基选自氢、氟、氯、溴、碘、氰基、硝基、羟基、(C1-C6)-烷基、(C1-C6)-烷氧基、羧基、被一个或多个相同或不同的卤原子取代的(C1-C6)-烷基、被一个或多个相同或不同的卤原子取代的(C1-C6)-烷氧基、直链或支链(C2-C6)-烯基、直链或支链(C2-C6)-炔基、(C3-C8)-环烷基、直链或支链(C1-C6)-烷氧基、直链或支链(C1-C6)-亚烷二氧基、直链或支链(C1-C6)-烷硫基、(C1-C4)-烷基亚磺酰基、(C1-C4)-烷基磺酰基、(C6-C14)-芳硫基、(C6-C14)-芳基亚磺酰基、(C6-C14)-芳基磺酰基、(C1-C6)-烷氧基-(C1-C6)-烷基、直链或支链单-(C1-C6)-烷基氨基、直链或支链二-(C1-C6)-烷基氨基—其中两个(C1-C4)基团一起可以构成可选含有一个或多个NH、N-(C1-C6)-烷基、O或S的环、(C6-C14)-芳基、(C6-C14)-芳氧基、(C6-C14)-芳基-(C1-C6)-烷基、(C6-C14)-芳基-(C1-C4)-烷氧基-(C1-C6)-烷基、(C1-C6)-烷基羰基、(C1-C6)-烷氧基羰基、直链或支链单-N-(C1-C6)-烷基羰基氨基、直链或支链二-N,N-(C1-C6)-烷基羰基氨基、直链或支链单-N-(C1-C6)-烷氧基羰基氨基、直链或支链二-N,N-(C1-C6)-烷氧基羰基氨基、直链或支链N-(C1-C6)-烷基羰基氨基-N-(C1-C6)-烷基氨基、直链或支链N-(C1-C6)-烷氧基羰基氨基-N-(C1-C6)-烷基氨基;
并且如果n=1,那么
Z是氮原子。
2、如权利要求1所要求保护的化合物,其特征在于R1是氢,R2、R3、R4和R5彼此独立为氢、卤素或(C1-C6)-烷氧基,R6是直链或支链(C1-C20)-烷基—未取代的或者被相同或不同的取代基完全或部分取代,或者是(C6-C14)-芳基—未取代的或者被相同或不同的取代基完全或部分取代,其取代基选自(C1-C6)-烷氧基和卤素,Y是氧原子或基团N-R7,其中R7是(C6-C14)-芳基—未取代的或者被相同或不同的取代基完全或部分取代,X是羰基(C=O),Z是氮原子且n=1。
3、如权利要求1所要求保护的化合物,其特征在于R1是氢,R2、R3、R4和R5彼此独立为氢、卤素或(C1-C6)-烷氧基,R6是直链或支链(C1-C20)-烷基—未取代的或者被相同或不同的取代基完全或部分取代,或者是(C6-C14)-芳基—未取代的或者被相同或不同的取代基完全或部分取代,其取代基选自(C1-C6)-烷氧基和卤素,n=0,Z是基团C-R8,其中R8是(C6-C14)-芳基—未取代的或者被相同或不同的取代基完全或部分取代,其取代基选自(C1-C6)-烷氧基和卤素且X是羰基(C=O)。
4、如权利要求1至3任一项所要求保护的化合物,其用作药物。
5、如权利要求1至3任一项所要求保护的化合物用于控制哺乳动物、特别是人类肿瘤病症的用途。
6、药物,其包含至少一种如权利要求1至3任一项所要求保护的化合物以及药学上可接受的辅助剂、稀释剂和/或载体。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE10143079A DE10143079A1 (de) | 2001-09-03 | 2001-09-03 | Cyclische Indol- und Heteroindolderivate, deren Herstellung und Verwendung als Arzneimittel |
DE10143079.5 | 2001-09-03 |
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CN1551885A true CN1551885A (zh) | 2004-12-01 |
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CNA028172639A Pending CN1551885A (zh) | 2001-09-03 | 2002-08-27 | 环状吲哚和杂吲哚衍生物、其作为药物的制备和用途 |
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EP (1) | EP1423393A1 (zh) |
JP (1) | JP2005508898A (zh) |
KR (1) | KR20040029463A (zh) |
CN (1) | CN1551885A (zh) |
AR (1) | AR036776A1 (zh) |
BR (1) | BR0212300A (zh) |
CA (1) | CA2458399A1 (zh) |
HU (1) | HUP0401446A3 (zh) |
IL (1) | IL160441A0 (zh) |
MX (1) | MXPA04002034A (zh) |
NO (1) | NO20040831L (zh) |
NZ (1) | NZ531642A (zh) |
PL (1) | PL370210A1 (zh) |
RU (1) | RU2004110412A (zh) |
ZA (1) | ZA200401290B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN111362891A (zh) * | 2020-04-01 | 2020-07-03 | 杭州福斯特药业有限公司 | 一种乙酰基四氢呋喃的生产装置及生产方法 |
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2002
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- 2002-08-27 IL IL16044102A patent/IL160441A0/xx unknown
- 2002-08-27 MX MXPA04002034A patent/MXPA04002034A/es unknown
- 2002-08-27 BR BR0212300-2A patent/BR0212300A/pt not_active IP Right Cessation
- 2002-08-27 KR KR10-2004-7003201A patent/KR20040029463A/ko not_active Application Discontinuation
- 2002-08-27 RU RU2004110412/04A patent/RU2004110412A/ru not_active Application Discontinuation
- 2002-08-27 CA CA002458399A patent/CA2458399A1/en not_active Abandoned
- 2002-08-27 PL PL02370210A patent/PL370210A1/xx not_active Application Discontinuation
- 2002-08-27 NZ NZ531642A patent/NZ531642A/en unknown
- 2002-08-27 JP JP2003525001A patent/JP2005508898A/ja not_active Withdrawn
- 2002-08-27 EP EP02767436A patent/EP1423393A1/de not_active Withdrawn
- 2002-08-27 CN CNA028172639A patent/CN1551885A/zh active Pending
- 2002-09-03 AR ARP020103329A patent/AR036776A1/es not_active Application Discontinuation
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN111362891A (zh) * | 2020-04-01 | 2020-07-03 | 杭州福斯特药业有限公司 | 一种乙酰基四氢呋喃的生产装置及生产方法 |
Also Published As
Publication number | Publication date |
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NZ531642A (en) | 2005-01-28 |
AR036776A1 (es) | 2004-10-06 |
KR20040029463A (ko) | 2004-04-06 |
IL160441A0 (en) | 2004-07-25 |
MXPA04002034A (es) | 2004-07-08 |
JP2005508898A (ja) | 2005-04-07 |
RU2004110412A (ru) | 2005-03-20 |
BR0212300A (pt) | 2004-10-13 |
PL370210A1 (en) | 2005-05-16 |
CA2458399A1 (en) | 2003-03-13 |
ZA200401290B (en) | 2004-03-23 |
EP1423393A1 (de) | 2004-06-02 |
NO20040831L (no) | 2004-04-13 |
HUP0401446A3 (en) | 2006-11-28 |
HUP0401446A2 (hu) | 2004-11-29 |
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