CN108912118A - A kind of tetrahydroisoquinoline and triazine framework compound and preparation method thereof - Google Patents
A kind of tetrahydroisoquinoline and triazine framework compound and preparation method thereof Download PDFInfo
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- CN108912118A CN108912118A CN201810760544.6A CN201810760544A CN108912118A CN 108912118 A CN108912118 A CN 108912118A CN 201810760544 A CN201810760544 A CN 201810760544A CN 108912118 A CN108912118 A CN 108912118A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
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Abstract
The present invention relates to compound synthesis field, a kind of tetrahydroisoquinoline and triazine framework compound and preparation method thereof are disclosed.The compound has the structural formula as shown in following formula (1).It according to the method described in the present invention can expeditiously tetrahydrobiopterin synthesis isoquinolin and triazine framework compound, and simultaneously triazine framework compound may be used as alkaloid to the tetrahydroisoquinoline, and it is active in terms of antitumor, antibacterial, antiviral, anti-inflammatory, anticoagulation, bronchiectasis and central nervous system.
Description
Technical field
The present invention relates to compound synthesis fields, and in particular to a kind of tetrahydroisoquinoline and triazine framework compound and its system
Preparation Method.
Background technique
Tetrahydroisoquinoline skeleton derivative is widely present in many with the active natural products of important biomolecule and drug point
In son, with significant application value and various pharmacological action in pharmaceutical chemistry, if any stronger anti-hypertension, the anti-rhythm of the heart
The effects of not normal, antithrombotic acitivity.Therefore it is very active grind that development, which efficiently synthesizes the new method of tetrahydro isoquinoline derivative,
Study carefully one of field.In recent years, tetrahydroisoquinolicompounds compounds are in antitumor, antibacterial, antiviral, anti-inflammatory, anticoagulation, bronchus
Expansion and central nervous system effect etc. are even more to achieve certain progress.Due to tetrahydroisoquinoliderivs derivs
Structure has diversity, can generate the drug action of multiplicity, if any stronger antithrombotic acitivity, anti-arrhythmia, anti-hypertension,
It also is the indispensable intermediate of gastric ulcer resistance medicine, and some also will affect skilful carrier frequency channel break and adrenocepter plays and makees
With.Therefore, its structure is transformed, modifies and is optimized via chemical synthesis tetrahydro isoquinoline compound structure diversity is weight
The approach wanted, while wide thinking can also be provided for the research and development of new drug.
Summary of the invention
It is described the purpose of the invention is to provide a kind of tetrahydroisoquinoline and triazine framework compound and preparation method thereof
Simultaneously triazine framework compound may be used as alkaloid to tetrahydroisoquinoline, in antitumor, antibacterial, antiviral, anti-inflammatory, anticoagulation, branch
Tracheaectasy and central nervous system effect etc. are active.
To achieve the goals above, one aspect of the present invention provides a kind of tetrahydroisoquinoline and triazine framework compound, the change
Closing object has the structural formula as shown in following formula (1),
Wherein, * is asymmetric carbon atom, R1For alkyl, alkoxy, H, F, Cl, Br, I, nitro, trifluoromethyl or fluoroform
Oxygroup；R2For benzyl, alkyl, acetyl group, tertbutyloxycarbonyl, benzoyl or benzyloxycarbonyl group；Ar is aryl, heterocyclic base, indoles
Base orSubstituted aryl, wherein R3、R4、R5、R6And R7It is each independently selected from H, F, Cl, Br, cyano, nitre
Base, trifluoromethyl, trifluoromethoxy, the oxyl of C1-C16 or C1-C16 alkyl.
Preferably, R1For the alkyl of C1-C6, the alkoxy of C1-C6, H, F, Cl, Br or I, R2For benzyl, the alkyl of C1-C6
Or benzyloxycarbonyl group, Ar are the aryl of C6-C18.
Most preferably, R1For H, R2For benzyl, Ar is phenyl.
Second aspect of the present invention provides a kind of tetrahydroisoquinoline shown in formula as previously described (1) and triazine skeleton of preparing
The method of compound, this method include：In presence of organic solvent, by C shown in formula (2), N- ring 1,3- dipole and formula
(3) N- methoxy-N- (trimethyl silane) fatty amine shown in carries out Dipolar Cycloaddition,
Wherein, R1、R2With Ar it is as defined above text described in.
According to the method described in the present invention can expeditiously tetrahydrobiopterin synthesis isoquinolin and triazine framework compound, the synthesis
Method is used without catalyst, and reaction condition is mild, easy to operate, wide application range of substrates, higher (the generally 92%- of yield
98%).
Moreover, simultaneously triazine framework compound may be used as alkaloid to tetrahydroisoquinoline of the present invention, antitumor, anti-
Bacterium, antiviral, anti-inflammatory, anticoagulation, bronchiectasis and central nervous system effect etc. are active.
Specific embodiment
The endpoint of disclosed range and any value are not limited to the accurate range or value herein, these ranges or
Value should be understood as comprising the value close to these ranges or value.For numberical range, between the endpoint value of each range, respectively
It can be combined with each other between the endpoint value of a range and individual point value, and individually between point value and obtain one or more
New numberical range, these numberical ranges should be considered as specific open herein.
Simultaneously triazine framework compound has the structural formula as shown in following formula (1) to tetrahydroisoquinoline of the present invention,
Wherein, * is asymmetric carbon atom, R1For alkyl, alkoxy, H, F, Cl, Br, I, nitro, trifluoromethyl or fluoroform
Oxygroup；R2For benzyl, alkyl, acetyl group, tertbutyloxycarbonyl, benzoyl or benzyloxycarbonyl group；Ar is aryl, heterocyclic base, indoles
Base orSubstituted aryl, wherein R3、R4、R5、R6And R7It is each independently selected from H, F, Cl, Br, cyano, nitre
Base, trifluoromethyl, trifluoromethoxy, the oxyl of C1-C16 or C1-C16 alkyl.
In formula (1), it is preferable that R1For the alkyl of C1-C6, the alkoxy of C1-C6, H, F, Cl, Br, I, nitro, trifluoro
Methyl or trifluoromethoxy.It is highly preferred that R1For the alkyl of C1-C6, the alkoxy of C1-C6, H, F, Cl, Br or I.C1-C6's
Alkyl for example can be methyl, ethyl, propyl, butyl, amyl or hexyl.The Alkoxy of C1-C6 such as can be methoxyl group, second
Oxygroup, propoxyl group, butoxy, amoxy or hexyloxy.
In formula (1), it is preferable that R2For benzyl, the alkyl of C1-C6, acetyl group, tertbutyloxycarbonyl, benzoyl or benzyl
Oxygen carbonyl.It is highly preferred that R2For benzyl, the alkyl or benzyloxycarbonyl group of C1-C6.The alkyl of C1-C6 for example can be methyl, second
Base, propyl, butyl, amyl or hexyl.
In formula (1), it is preferable that Ar be the aryl of C6-C18, the heterocyclic base of C6-C18, indyl or
Substituted C6-C18 aryl, wherein R3、R4、R5、R6And R7Be each independently selected from H, F, Cl, Br, cyano, nitro, trifluoromethyl,
The alkyl of trifluoromethoxy, the oxyl of C1-C16 or C1-C16.It is highly preferred that Ar is the aryl of C6-C18, such as can be
Substituted or unsubstituted phenyl, substituent group are methyl, halogen (such as Cl or Br) or nitro.
In a preferred embodiment, in formula (1), R1For the alkyl of C1-C6, the alkoxy of C1-C6, H, F, Cl,
Br or I, R2For benzyl, the alkyl or benzyloxycarbonyl group of C1-C6, Ar is the aryl of C6-C18.Most preferably, R1For H, R2For benzyl
(Bn), Ar is substituted or unsubstituted phenyl, and substituent group is methyl, halogen (such as Cl or Br) or nitro.
The preparation method of tetrahydroisoquinoline of the present invention and triazine framework compound includes：In the presence of organic solvent
Under, by C shown in formula (2), N- ring 1,3- dipole and the fat of N- methoxy-N- (trimethyl silane) shown in formula (3)
Amine carries out Dipolar Cycloaddition,
Wherein, R1、R2With Ar it is as defined above text described in.
Herein, Me refers to that methyl, TMS refer to trimethylsilyl.
In method of the present invention, it is preferable that the Dipolar Cycloaddition carries out in the presence of trifluoroacetic acid.
In the present invention, the reaction route of the Dipolar Cycloaddition is as follows.
In method of the present invention, C, N- ring 1,3- dipole, N- methoxy-N- (trimethyl silane) fat
The molar ratio of amine and trifluoroacetic acid can be 1：(1-2)：(1-2), preferably 1：(1.2-1.8)：(1.2-1.8), more preferably
1：(1.3-1.6)：(1.3-1.6).
In method of the present invention, the reaction condition of the Dipolar Cycloaddition may include：Temperature is 0-50
DEG C, time 12-48h.
In method of the present invention, the organic solvent can be the conventional selection of this field, such as can be second
Nitrile, toluene, methylene chloride, chloroform, tetrahydrofuran, ethyl acetate, acetone, ether, dioxane, dimethylbenzene, benzene, diformazan
At least one of sulfoxide and formamide.
In method of the present invention, reaction product (i.e. tetrahydroisoquinoline shown in target product formula (1) and triazine bone
Frame compound) it can be separated by the method that column chromatographs.Solvent used in separation process can be polar solvent and non-
The mixed solvent of the mixed solvent of polar solvent, preferably petroleum ether and ethyl acetate.In the mixing of petroleum ether and ethyl acetate
In solvent, the mass ratio of petroleum ether and ethyl acetate can be 1：3-5.
Method of the present invention is a kind of with stable 1,3- dipole and N- methoxy-N- (trimethyl silane)
Fatty amine, expeditiously synthesis has [3+3] cycloaddition product of multi-functional functional group.The synthetic method is used without catalyst,
Reaction condition is mild, easy to operate, wide application range of substrates, and yield is also higher (generally 92%-98%), and the change synthesized
Closing object has tetrahydroisoquinoline and triazine skeleton.
The present invention will be described in detail by way of examples below, but protection scope of the present invention is not limited to that.
In following embodiment, N- methoxy-N- (trimethyl silane) fatty amine, which is purchased from Beijing lark prestige science and technology, to be had
Limit company.
Embodiment 1
C shown in formula (2-1), N- ring 1,3- dipole (1mmol), formula (3- are sequentially added in clean round-bottomed flask
1) N- methoxy-N- (trimethyl silane) fatty amine (1mmol), trifluoroacetic acid (1mmol) and methylene chloride shown in
Reaction 24 hours is stirred at room temperature in 10mL, merging, and using the mixed solvent of petroleum ether and ethyl acetate, (the two mass ratio is 1：5) into
Row column chromatography, isolated product, product yield 96%.
The nuclear magnetic resonance data and mass spectrometric data of products therefrom are as follows：
1H NMR(400MHz,CDCl3) δ 7.61 (d, J=7.2Hz, 2H), 7.41-7.28 (m, 8H), 7.13-7.09 (m,
2H), 7.03 (d, J=7.2Hz, 1H), 6.88 (d, J=6.4Hz, 1H), 5.28 (d, J=11.2Hz, 1H), 4.49 (dd, J=
10.4,3.6Hz, 1H), 3.84 (dd, J=22.4,12.4Hz, 2H), 3.77-3.68 (m, 2H), 2.92-2.85 (m, 2H),
2.80 (t, J=8.4Hz, 2H), 2.65 (d, J=16.0Hz, 1H)
13C NMR(100MHz,CDCl3)δ171.6,136.9,135.4,135.1,133.6,129.8,129.1,128.7,
128.5,127.9,127.44,127.42,126.8,126.7,125.9,58.5,56.5,55.3,51.8,43.9,29.3.
High resolution mass spectrum calculating value：C25H25N3O+Na+406.1890, measured value：406.1891.
It is possible thereby to estimate, shown in the structural formula of products therefrom such as following formula (1-1),
Embodiment 2
C shown in formula (2-2), N- ring 1,3- dipole (1mmol), formula (3- are sequentially added in clean round-bottomed flask
1) N- methoxy-N- (trimethyl silane) fatty amine (1mmol), trifluoroacetic acid (1mmol) and methylene chloride shown in
Reaction 24 hours is stirred at room temperature in 10mL, merging, and using the mixed solvent of petroleum ether and ethyl acetate, (the two mass ratio is 1：4) into
Row column chromatography, isolated product, product yield 95%.
The nuclear magnetic resonance data and mass spectrometric data of products therefrom are as follows：
1H NMR(400MHz,CDCl3) δ 7.56 (d, J=7.6Hz, 2H), 7.42-7.35 (m, 4H), 7.32-7.29 (m,
1H), 7.15-7.08 (m, 4H), 7.05 (d, J=6.8Hz, 1H), 6.89 (d, J=6.8Hz, 1H), 5.28 (d, J=11.6Hz,
1H), 4.49 (d, J=6.4Hz, 1H), 3.88-3.70 (m, 4H), 2.93-2.90 (m, 2H), 2.85-2.76 (m, 2H), 2.68
(d, J=15.2Hz, 1H), 2.33 (s, 3H)
13C NMR(100MHz,CDCl3)δ171.5,140.1,136.9,135.2,133.7,132.2,129.2,128.7,
128.5,128.3,128.1,127.4,126.8,126.7,125.9,58.6,56.4,55.3,51.8,43.8,29.3,21.4.
High resolution mass spectrum calculating value：C26H27N3O+Na+420.2046, measured value：420.2047.
It is possible thereby to estimate, shown in the structural formula of products therefrom such as following formula (1-2),
Embodiment 3
C shown in formula (2-3), N- ring 1,3- dipole (1mmol), formula (3- are sequentially added in clean round-bottomed flask
1) N- methoxy-N- (trimethyl silane) fatty amine (1mmol), trifluoroacetic acid (1mmol) and methylene chloride shown in
Reaction 24 hours is stirred at room temperature in 10mL, merging, and using the mixed solvent of petroleum ether and ethyl acetate, (the two mass ratio is 1：5) into
Row column chromatography, isolated product, product yield 95%.
The nuclear magnetic resonance data and mass spectrometric data of products therefrom are as follows：
1H NMR(400MHz,CDCl3) δ 7.52 (d, J=7.6Hz, 2H), 7.45 (d, J=7.6Hz, 2H), 7.38-7.37
(m, 4H), 7.32 (d, J=5.6Hz, 1H), 7.12-7.06 (m, 2H), 6.90 (d, J=6.0Hz, 1H), 5.24 (d, J=
11.6Hz, 1H), 4.47 (d, J=8.4Hz, 1H), 3.87-3.70 (m, 4H), 2.88-2.79 (m, 4H), 2.69 (d, J=
15.6Hz,1H).
13C NMR(100MHz,CDCl3)δ170.4,136.7,134.8,134.0,133.4,130.6,129.8,129.1,
128.8,128.5,127.5,126.9,126.7,126.0,124.3,58.6,56.6,55.4,51.8,43.9,29.3.
High resolution mass spectrum calculating value：C25H24BrN3O+Na+484.0995, measured value：484.0996.
It is possible thereby to estimate, shown in the structural formula of products therefrom such as following formula (1-3),
Embodiment 4
C shown in formula (2-4), N- ring 1,3- dipole (1mmol), formula (3- are sequentially added in clean round-bottomed flask
1) N- methoxy-N- (trimethyl silane) fatty amine (1mmol), trifluoroacetic acid (1mmol) and methylene chloride shown in
Reaction 24 hours is stirred at room temperature in 10mL, merging, and using the mixed solvent of petroleum ether and ethyl acetate, (the two mass ratio is 1：4) into
Row column chromatography, isolated product, product yield 96%.
The nuclear magnetic resonance data and mass spectrometric data of products therefrom are as follows：
1H NMR(400MHz,CDCl3) δ 8.18 (d, J=8.4Hz, 2H), 7.72 (d, J=8.4Hz, 2H), 7.41-7.36
(m, 4H), 7.33-7.32 (m, 1H), 7.15-7.09 (m, 2H), 7.03 (d, J=7.6Hz, 1H), 6.89 (d, J=6.8Hz,
1H), 5.23 (d, J=11.6Hz, 1H), 4.43 (dd, J=11.2,3.6Hz, 1H), 3.83 (dd, J=18.6,12.4Hz,
2H), 3.77-3.71 (m, 2H), 2.90-2.84 (m, 2H), 2.82-2.74 (m, 2H), 2.68 (d, J=14.0Hz, 1H)
13C NMR(100MHz,CDCl3)δ169.6,148.2,142.1,136.5,134.4,133.1,129.1,128.8,
128.6,128.4,127.6,127.1,126.7,126.1,122.9,58.7,56.9,55.4,51.9,44.1,29.2.
High resolution mass spectrum calculating value：C25H24N4O3+Na+451.1741, measured value：451.1741.
It is possible thereby to estimate, shown in the structural formula of products therefrom such as following formula (1-4),
The preferred embodiment of the present invention has been described above in detail, and still, the present invention is not limited thereto.In skill of the invention
In art conception range, can with various simple variants of the technical solution of the present invention are made, including each technical characteristic with it is any its
Its suitable method is combined, and it should also be regarded as the disclosure of the present invention for these simple variants and combination, is belonged to
Protection scope of the present invention.
Claims (10)
1. a kind of tetrahydroisoquinoline and triazine framework compound, which has the structural formula as shown in following formula (1),
Wherein, * is asymmetric carbon atom, R1For alkyl, alkoxy, H, F, Cl, Br, I, nitro, trifluoromethyl or trifluoromethoxy；
R2For benzyl, alkyl, acetyl group, tertbutyloxycarbonyl, benzoyl or benzyloxycarbonyl group；Ar be aryl, heterocyclic base, indyl orSubstituted aryl, wherein R3、R4、R5、R6And R7It is each independently selected from H, F, Cl, Br, cyano, nitro, three
Methyl fluoride, trifluoromethoxy, the oxyl of C1-C16 or C1-C16 alkyl.
2. compound according to claim 1, which is characterized in that R1For the alkyl of C1-C6, the alkoxy of C1-C6, H, F,
Cl, Br or I, R2For benzyl, the alkyl or benzyloxycarbonyl group of C1-C6, Ar is the aryl of C6-C18.
3. compound according to claim 1, which is characterized in that R1For H, R2For benzyl, Ar is substituted or unsubstituted benzene
Base, substituent group are methyl, halogen or nitro.
4. a kind of method for preparing tetrahydroisoquinoline shown in formula as described in claim 1 (1) and triazine framework compound, should
Method includes：In presence of organic solvent, by C shown in formula (2), N- ring 1,3- dipole and N- methoxy shown in formula (3)
Ylmethyl-N- (trimethyl silane) fatty amine carries out Dipolar Cycloaddition,
Wherein, R1、R2It is as described in claim 1 with the definition of Ar.
5. according to the method described in claim 4, it is characterized in that, the Dipolar Cycloaddition is in the presence of trifluoroacetic acid
It carries out.
6. according to the method described in claim 5, it is characterized in that, C, N- ring 1,3- dipole, N- methoxy-N- (three
Methyl-monosilane) molar ratio of fatty amine and trifluoroacetic acid is 1：(1-2)：(1-2).
7. method according to any one of claims 4 to 6, which is characterized in that the reaction of the Dipolar Cycloaddition
Condition includes：Temperature is 0-50 DEG C, time 12-48h.
8. method according to any one of claims 4 to 6, which is characterized in that the organic solvent be acetonitrile, toluene,
Methylene chloride, chloroform, tetrahydrofuran, ethyl acetate, acetone, ether, dioxane, dimethylbenzene, benzene, dimethyl sulfoxide and first
At least one of amide.
9. method according to any one of claims 4 to 6, which is characterized in that the method that reaction product is chromatographed by column
It is separated.
10. according to the method described in claim 9, it is characterized in that, solvent used in separation process is petroleum ether and acetic acid
The mixed solvent of ethyl ester.
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Citations (4)
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| CN1324359A (en) * | 1998-08-05 | 2001-11-28 | 史密丝克莱恩比彻姆有限公司 | Tricyclic carboxamides |
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| CN101484190A (en) * | 2006-05-02 | 2009-07-15 | 宾夕法尼亚大学理事会 | Radiolabeled dihydrotetrabenazine derivatives and their use as imaging agents |
| KR20140046808A (en) * | 2012-10-11 | 2014-04-21 | 한국화학연구원 | Compositions for prevention or treating hyperproliferative vascular disorders |
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2018
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP3794448B2 (en) * | 1998-02-16 | 2006-07-05 | 塩野義製薬株式会社 | Reagent for detection of ruthenium complexes of carboxylic acids containing benzoquinolizidine derivatives |
| CN1324359A (en) * | 1998-08-05 | 2001-11-28 | 史密丝克莱恩比彻姆有限公司 | Tricyclic carboxamides |
| CN101484190A (en) * | 2006-05-02 | 2009-07-15 | 宾夕法尼亚大学理事会 | Radiolabeled dihydrotetrabenazine derivatives and their use as imaging agents |
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