Novel p-coumaric acid sulfonate derivative, preparation method and application thereof

A kind of technology of coumaric acid sulfonate and p-coumaric acid, applied in the field of novel p-coumaric acid sulfonate derivative and preparation thereof

Pending Publication Date: 2019-12-31
南京施倍泰生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there is a lack of a new class of p-coumaric acid sulfonate derivatives an

Method used

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  • Novel p-coumaric acid sulfonate derivative, preparation method and application thereof
  • Novel p-coumaric acid sulfonate derivative, preparation method and application thereof
  • Novel p-coumaric acid sulfonate derivative, preparation method and application thereof

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Embodiment 1

[0024] A class of novel p-coumaric acid sulfonate derivatives of the present invention, the structural formula of described novel p-coumaric acid sulfonate derivatives is as shown in formula (I):

[0025]

[0026] Wherein, R is selected from:

[0027] The synthetic process of a class of novel p-coumaric acid sulfonate derivatives of the present invention, it has following general formula:

[0028]

[0029] Wherein, R is selected from:

[0030] The preparation method of described a class of novel p-coumaric acid sulfonate derivatives of the present invention, comprises the steps:

[0031] Dissolve p-coumaric acid in dichloromethane, add various sulfonyl chlorides, stir for 20 min under ice-bath conditions, add 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride and 1-Hydroxybenzotriazole, move to room temperature and stir for 12 hours, follow the reaction by thin layer chromatography, filter the precipitate after the reaction, extract the filtrate with an ext...

Embodiment 2

[0039] The difference between embodiment 2 and embodiment 1 is:

[0040] The preparation method of described a class of novel p-coumaric acid sulfonate derivatives of the present invention, comprises the steps:

[0041] Dissolve p-coumaric acid in dichloromethane, add various sulfonyl chlorides, stir for 40 min under ice-bath conditions, add 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride and 1-Hydroxybenzotriazole, move to room temperature and stir for 4 hours, follow the reaction by thin-layer chromatography, filter the precipitate after the reaction, extract the filtrate with an extractant, wash with saturated sodium chloride solution, and distill under reduced pressure Remove the organic solvent, and use the mixed solvent of acetone and ethanol to recrystallize to obtain a new type of p-coumaric acid sulfonate derivatives.

[0042] The extractant is dichloromethane, and the number of washings of the saturated sodium chloride solution is 4 times.

Embodiment 3

[0044] The difference between embodiment 3 and embodiment 1 is:

[0045] The preparation method of described a class of novel p-coumaric acid sulfonate derivatives of the present invention, comprises the steps:

[0046] Dissolve p-coumaric acid in dichloromethane, add various sulfonyl chlorides, stir for 30 min under ice-bath conditions, add 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride and 1-Hydroxybenzotriazole, move to room temperature and stir for 8 hours, follow the reaction by thin layer chromatography, filter the precipitate after the reaction, extract the filtrate with extractant, wash with saturated sodium chloride solution, and distill under reduced pressure Remove the organic solvent, and use the mixed solvent of acetone and ethanol to recrystallize to obtain a new type of p-coumaric acid sulfonate derivatives.

[0047] The extractant is dichloromethane, and the number of washings of the saturated sodium chloride solution is 6 times.

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Abstract

The invention discloses a novel p-coumaric acid sulfonate derivative, a preparation method and application thereof. The structural formula of the novel p-coumaric acid sulfonate derivative is shown asformula (I) in the specification, wherein R is selected from the following groups shown as the specification. The compound provided by the invention has potential pharmaceutical activity, and the preparation raw material p-coumaric acid can be obtained by natural extraction method, thus having a positive effect on resource utilization of spartina alterniflora.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a novel p-coumaric acid sulfonate derivative and its preparation method and application. Background technique [0002] P-coumaric acid is an important class of hydroxycinnamic acid compounds, which have been reported to have anti-oxidant, antibacterial, and therapeutic activities for cardiovascular diseases. At present, the production methods of p-coumaric acid mainly include chemical synthesis, natural extraction, and biotransformation. Considering the risk of environmental pollution and the stability of the production source, the natural extraction method is the technology that is most in line with the concept of environmental protection and quality control. means. Sulfonate derivatization is a feasible solution in drug modification, which has a positive effect on the improvement of drug properties. Common sulfonate drugs such as busulfan and sulfonate mucopolysacc...

Claims

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Application Information

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IPC IPC(8): C07C303/28C07C309/65A01N41/04A61P39/06A61P31/04A61P31/10A61P9/00A01P13/00
CPCC07C309/65A01N41/04A61P39/06A61P31/04A61P31/10A61P9/00
Inventor 李玉广钦佩杨雨顺方莉陈利丽
Owner 南京施倍泰生物科技有限公司
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