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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- 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
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- 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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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 |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
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| CN109534984A (en) * | 2018-12-19 | 2019-03-29 | 南京大学 | A method of p-Coumaric Acid is prepared using Spartina alterniflora |
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2019
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| 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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