CN110627690A - Novel p-coumaric acid sulfonate derivative and preparation method and application thereof - Google Patents
Novel p-coumaric acid sulfonate derivative and preparation method and application thereof Download PDFInfo
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- CN110627690A CN110627690A CN201910946228.2A CN201910946228A CN110627690A CN 110627690 A CN110627690 A CN 110627690A CN 201910946228 A CN201910946228 A CN 201910946228A CN 110627690 A CN110627690 A CN 110627690A
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- NGSWKAQJJWESNS-UHFFFAOYSA-N cis-para-coumaric acid Natural products OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 title claims abstract description 62
- NGSWKAQJJWESNS-ZZXKWVIFSA-M 4-Hydroxycinnamate Natural products OC1=CC=C(\C=C\C([O-])=O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-M 0.000 title claims abstract description 49
- DFYRUELUNQRZTB-UHFFFAOYSA-N Acetovanillone Natural products COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 title claims abstract description 49
- -1 p-coumaric acid sulfonate derivative Chemical class 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 241001149258 Sporobolus alterniflorus Species 0.000 claims abstract description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 11
- 238000005406 washing Methods 0.000 claims description 11
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000012046 mixed solvent Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 6
- 238000004809 thin layer chromatography Methods 0.000 claims description 6
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 4
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 4
- 238000000605 extraction Methods 0.000 abstract description 7
- 239000002253 acid Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 5
- 230000008092 positive effect Effects 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 241000245565 Sporobolus anglicus Species 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000001212 derivatisation Methods 0.000 description 2
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 2
- 229910000071 diazene Inorganic materials 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 229920002683 Glycosaminoglycan Polymers 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 229960002092 busulfan Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229930005346 hydroxycinnamic acid Natural products 0.000 description 1
- 235000010359 hydroxycinnamic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biochemistry (AREA)
- Toxicology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a novel p-coumaric acid sulfonate derivative and a preparation method and application thereof. The invention relates to novel p-coumaric acid sulfonate derivatives, the structural formula of which is shown as formula (I)：Wherein R is selected from:
Description
Technical Field
The invention relates to the technical field of medicinal chemistry, in particular to novel p-coumaric acid sulfonate derivatives and a preparation method and application thereof.
Background
P-coumaric acid is an important hydroxycinnamic acid compound and has been reported to have activities of resisting oxidation, resisting bacteria, treating cardiovascular diseases and the like. At present, the production method of coumaric acid mainly comprises chemical synthesis, natural extraction, biotransformation and the like, the risk of environmental pollution caused by coumaric acid and the stability of coumaric acid serving as a production source are comprehensively considered, and the natural extraction method is the technical means which most accords with the concepts of environmental protection and quality control. Sulfonate derivatization is a feasible scheme in drug modification, has positive effect on drug attribute improvement, and is common sulfonate drugs such as busulfan, sulfonate mucopolysaccharide and the like.
The spartina alterniflora is a perennial high-stalk herbaceous plant of gramineae, is introduced into China by professor Zhongchong letter of Nanjing university at the end of 1979, and is successfully introduced into coastal areas of China in 80-90 years of the 20 th century, thereby making great contribution to beach protection and silt promotion and land building in coastal areas of China. But its growth spread has also affected the biodiversity and ecological environment of some coastal areas. Because the plants are higher and the yield is higher, the traditional treatment means such as harvesting and the like need to invest certain cost, the resource utilization of the spartina alterniflora is realized, the raw materials are stably produced by a natural extraction method, and then functional molecules with potential medicinal activity are developed, so that the huge economic benefit can be generated, and the good ecological effect can be brought. Taking scientific researchers in halophyte laboratories of Nanjing university as a representative, the edibility of the spartina alterniflora extract (new resource food of Ministry of health, Weixin food Standard No. 94, No. 06) has been solved internationally at present.
At present, a novel p-coumaric acid sulfonate derivative for realizing the resource utilization of spartina anglica and a preparation method and application thereof are lacked.
Disclosure of Invention
The invention aims to provide novel p-coumaric acid sulfonate derivatives for realizing the resource utilization of spartina anglica, and a preparation method and application thereof.
The technical scheme of the invention is as follows: the structural formula of the novel p-coumaric acid sulfonate derivative is shown as the formula (I):
wherein R is selected from:
the invention relates to a synthetic process of a novel p-coumaric acid sulfonate derivative, which has the following general formula:
wherein R is selected from:
the preparation method of the novel p-coumaric acid sulfonate derivative comprises the following steps:
dissolving p-coumaric acid in dichloromethane, adding a plurality of sulfonyl chlorides, stirring for 20-40min under an ice bath condition, adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and 1-hydroxybenzotriazole, moving to room temperature, stirring for 4-12h, carrying out thin-layer chromatography tracking reaction, filtering a precipitate after the reaction is finished, extracting a filtrate by using an extracting agent, washing by using a saturated sodium chloride solution, carrying out reduced pressure distillation to remove an organic solvent, and recrystallizing by using a mixed solvent of acetone and ethanol to prepare the novel p-coumaric acid sulfonate derivative.
Further, the molar volume ratio of p-coumaric acid to dichloromethane is 1 mmol: 10 mL.
Further, the molar ratio of the p-coumaric acid, the sulfonyl chloride, the 1-ethyl- (3-dimethylaminopropyl) carbonyldiimine hydrochloride and the 1-hydroxybenzotriazole is 1: 1: 1.5: 0.5.
furthermore, the volume ratio of the acetone to the ethanol is 1: 5.
Further, the extracting agent is ethyl acetate or dichloromethane.
Further, the number of washing times of the saturated sodium chloride solution is 3 or more.
The invention relates to application of a novel p-coumaric acid sulfonate derivative in spartina alterniflora resource utilization. As the spartina alterniflora is generally considered as an invasive species, the spartina alterniflora is not used for extraction and also needs to be managed and controlled; the raw materials and products are obtained by a natural extraction method, so that the spartina alterniflora is recycled, and the property of changing waste into valuable is achieved.
The invention relates to application of a novel p-coumaric acid sulfonate derivative in preparation of a medicament.
Has the advantages that: the preparation raw material of the coumaric acid sulfonate derivative can be obtained by a natural extraction method, and has a positive effect on realizing resource utilization of spartina alterniflora. The obtained p-coumaric acid sulfonate derivative has potential pharmaceutical activity. Sulfonate derivatization is a feasible scheme in drug modification, and has a positive effect on the improvement of drug properties.
Detailed Description
The invention is further illustrated by the following examples. It should be understood that these examples are illustrative and exemplary of the present invention, and are not intended to limit the scope of the present invention in any way.
Example 1
The structural formula of the novel p-coumaric acid sulfonate derivative is shown as the formula (I):
wherein R is selected from:
the invention relates to a synthetic process of a novel p-coumaric acid sulfonate derivative, which has the following general formula:
wherein R is selected from:
the preparation method of the novel p-coumaric acid sulfonate derivative comprises the following steps:
dissolving p-coumaric acid in dichloromethane, adding various sulfonyl chlorides, stirring for 20min under an ice bath condition, adding 1-ethyl- (3-dimethylaminopropyl) carbonyldiimine hydrochloride and 1-hydroxybenzotriazole, moving to room temperature, stirring for 12h, carrying out thin-layer chromatography tracking reaction, filtering precipitates after the reaction is finished, extracting a filtrate by using an extracting agent, washing by using a saturated sodium chloride solution, carrying out reduced pressure distillation to remove an organic solvent, and recrystallizing by using a mixed solvent of acetone and ethanol to obtain the novel p-coumaric acid sulfonate derivative.
The mol volume ratio of p-coumaric acid to dichloromethane is 1 mmol: 10 mL.
The molar ratio of the p-coumaric acid, the sulfonyl chloride, the 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and the 1-hydroxybenzotriazole is 1: 1: 1.5: 0.5.
the volume ratio of the acetone to the ethanol is 1: 5.
The extractant is ethyl acetate, and the washing times of the saturated sodium chloride solution are 3 times.
The invention relates to application of a novel p-coumaric acid sulfonate derivative in spartina alterniflora resource utilization.
The invention relates to application of a novel p-coumaric acid sulfonate derivative in preparation of a medicament.
Example 2
Example 2 differs from example 1 in that:
the preparation method of the novel p-coumaric acid sulfonate derivative comprises the following steps:
dissolving p-coumaric acid in dichloromethane, adding various sulfonyl chlorides, stirring for 40min under an ice bath condition, adding 1-ethyl- (3-dimethylaminopropyl) carbonyldiimine hydrochloride and 1-hydroxybenzotriazole, moving to room temperature, stirring for 4h, carrying out thin-layer chromatography tracking reaction, filtering precipitates after the reaction is finished, extracting a filtrate by using an extracting agent, washing by using a saturated sodium chloride solution, carrying out reduced pressure distillation to remove an organic solvent, and recrystallizing by using a mixed solvent of acetone and ethanol to obtain the novel p-coumaric acid sulfonate derivative.
The extractant is dichloromethane, and the washing times of the saturated sodium chloride solution are 4 times.
Example 3
Example 3 differs from example 1 in that:
the preparation method of the novel p-coumaric acid sulfonate derivative comprises the following steps:
dissolving p-coumaric acid in dichloromethane, adding various sulfonyl chlorides, stirring for 30min under an ice bath condition, adding 1-ethyl- (3-dimethylaminopropyl) carbonyl diimine hydrochloride and 1-hydroxybenzotriazole, moving to room temperature, stirring for 8h, carrying out thin-layer chromatography tracking reaction, filtering precipitates after the reaction is finished, extracting a filtrate by using an extracting agent, washing by using a saturated sodium chloride solution, carrying out reduced pressure distillation to remove an organic solvent, and recrystallizing by using a mixed solvent of acetone and ethanol to obtain the novel p-coumaric acid sulfonate derivative.
The extractant is dichloromethane, and the washing times of the saturated sodium chloride solution are 6 times.
Example 4
Preparation of 3- (4- ((ethylsulfonyl) oxy) phenyl) acrylic acid:
dissolving p-coumaric acid (1mmol) in 10mL dichloromethane, adding ethylsulfonyl chloride (1mmol), stirring for 40min under an ice bath condition, adding 1-ethyl- (3-dimethylaminopropyl) carbonyl diimine hydrochloride (1.5mmol) and 1-hydroxybenzotriazole (0.5mmol), moving to room temperature, stirring for 4h, tracking the reaction by thin layer chromatography, filtering the precipitate after the reaction is finished, extracting the filtrate by using an extracting agent, washing by using a saturated sodium chloride solution, removing the organic solvent by reduced pressure distillation, and recrystallizing by using a mixed solvent of acetone and ethanol in a volume ratio of 1:5 to prepare the novel p-coumaric acid sulfonate derivative.
Obtaining light yellow powder with melting point of 185-187 ℃; the yield is 25 percent;1H NMR(600MHz,DMSO-d6)δ12.05(s,1H),7.69(d,J＝8.1Hz,2H),7.45(d,J＝8.4Hz,1H),7.24(d,J＝7.2Hz,2H),6.45(d,J＝8.7Hz,1H),3.21(q,J＝7.2Hz,2H),1.34(t,J＝7.5Hz,3H).HRMS(ESI-TOF)m/z:[M+H]+Calcd for C11H13O5S 257.0483,Found 257.0479.
example 5
Preparation of 3- (4- ((isopropylsulfonyl) oxy) phenyl) acrylic acid:
the preparation method refers to example 4.
Obtaining light yellow powder with melting point of 197 ℃ and 198 ℃; the yield is 33%;1H NMR(600MHz,DMSO-d6)δ12.08(s,1H),7.72(d,J＝7.8Hz,2H),7.47(d,J＝8.1Hz,1H),7.27(d,J＝7.5Hz,2H),6.48(d,J＝8.7Hz,1H),3.28(m,1H),1.45(d,J＝7.2Hz,6H).HRMS(ESI-TOF)m/z:[M+H]+Calcd for C12H15O5S 271.0640,Found 271.0642.
example 6
Preparation of 3- (4- ((propylsulfonyl) oxy) phenyl) acrylic acid:
the preparation method refers to example 4.
Obtaining light yellow powder with a melting point of 189-; the yield is 28 percent;1H NMR(600MHz,DMSO-d6)δ12.06(s,1H),7.70(d,J＝7.5Hz,2H),7.44(d,J＝8.1Hz,1H),7.25(d,J＝7.8Hz,2H),6.46(d,J＝8.7Hz,1H),3.23(t,J＝7.2Hz,2H),1.87(m,2H),1.33(t,J＝7.5Hz,3H).HRMS(ESI-TOF)m/z:[M+H]+Calcd for C12H15O5S 271.0640,Found271.0643.
the specific embodiments described herein are merely illustrative of the spirit of the invention. Various modifications or additions may be made to the described embodiments or alternatives may be employed by those skilled in the art without departing from the spirit or ambit of the invention as defined in the appended claims.
Claims (9)
1. A novel p-coumaric acid sulfonate derivative is characterized in that: the structural formula of the novel p-coumaric acid sulfonate derivative is shown as the formula (I):
wherein R is selected from:
2. the process for preparing a novel group of p-coumaric acid sulfonate derivatives according to claim 1, characterized by comprising the following steps:
dissolving p-coumaric acid in dichloromethane, adding a plurality of sulfonyl chlorides, stirring for 20-40min under an ice bath condition, adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and 1-hydroxybenzotriazole, moving to room temperature, stirring for 4-12h, carrying out thin-layer chromatography tracking reaction, filtering a precipitate after the reaction is finished, extracting a filtrate by using an extracting agent, washing by using a saturated sodium chloride solution, carrying out reduced pressure distillation to remove an organic solvent, and recrystallizing by using a mixed solvent of acetone and ethanol to prepare the novel p-coumaric acid sulfonate derivative.
3. The process for preparing a novel group of p-coumaric acid sulfonate derivatives according to claim 2, characterized in that: the mol volume ratio of p-coumaric acid to dichloromethane is 1 mmol: 10 mL.
4. The process for preparing a novel group of p-coumaric acid sulfonate derivatives according to claim 2, characterized in that: the molar ratio of the p-coumaric acid, the sulfonyl chloride, the 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and the 1-hydroxybenzotriazole is 1: 1: 1.5: 0.5.
5. the process for preparing a novel group of p-coumaric acid sulfonate derivatives according to claim 2, characterized in that: the volume ratio of the acetone to the ethanol is 1: 5.
6. The process for preparing a novel group of p-coumaric acid sulfonate derivatives according to claim 2, characterized in that: the extractant is ethyl acetate or dichloromethane.
7. The process for preparing a novel group of p-coumaric acid sulfonate derivatives according to claim 2, characterized in that: the washing times of the saturated sodium chloride solution are more than 3 times.
8. Use of the novel p-coumaric acid sulfonate derivative according to any one of claims 1 to 7 for the resource utilization of spartina alterniflora.
9. Use of a novel p-coumaric acid sulfonate derivative according to any one of claims 1 to 7 for the preparation of a medicament.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114685323A (en) * | 2022-04-24 | 2022-07-01 | 南京大学 | Cinnamic amide structure-based sulfophenol ester derivatives and preparation method and application thereof |
| CN114702414A (en) * | 2022-04-24 | 2022-07-05 | 南京大学 | Phenylacryloyl acid ester derivatives containing n-butyl sulfonate structure and preparation method and application thereof |
| CN114773237A (en) * | 2022-04-24 | 2022-07-22 | 南京大学 | Novel phenylpropenyl hydroximic acid derivatives containing sulfonate structure, and preparation method and application thereof |
| CN114773238A (en) * | 2022-04-24 | 2022-07-22 | 南京大学 | Phenylacryloyl acylated p-chlorophenyl sulfonyl ferulic acid ester derivatives, and preparation method and application thereof |
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Cited By (6)
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| CN114685323A (en) * | 2022-04-24 | 2022-07-01 | 南京大学 | Cinnamic amide structure-based sulfophenol ester derivatives and preparation method and application thereof |
| CN114702414A (en) * | 2022-04-24 | 2022-07-05 | 南京大学 | Phenylacryloyl acid ester derivatives containing n-butyl sulfonate structure and preparation method and application thereof |
| CN114773237A (en) * | 2022-04-24 | 2022-07-22 | 南京大学 | Novel phenylpropenyl hydroximic acid derivatives containing sulfonate structure, and preparation method and application thereof |
| CN114773238A (en) * | 2022-04-24 | 2022-07-22 | 南京大学 | Phenylacryloyl acylated p-chlorophenyl sulfonyl ferulic acid ester derivatives, and preparation method and application thereof |
| CN114685323B (en) * | 2022-04-24 | 2023-01-06 | 南京大学 | Cinnamic amide structure-based sulfophenol ester derivatives and preparation method and application thereof |
| CN114702414B (en) * | 2022-04-24 | 2023-03-10 | 南京大学 | Phenylacryloyl acid ester derivatives containing n-butyl sulfonate structure and preparation method and application thereof |
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