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Novel ferulic acid sulfonate derivative and preparation method and application thereof

A technology of ferulic acid sulfonic acid esters and derivatives, which is applied in the preparation of sulfonic acid esters, sulfuric acid amides, organic chemistry, etc., can solve the problems of lack of preparation methods of ferulic acid sulfonic acid ester derivatives and the like

Pending Publication Date: 2019-12-20
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

[0005] At present, there is a lack of a class of ferulic acid sulfonate derivatives for resource utilization of Spartina and its preparation method and application

Method used

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  • Novel ferulic acid sulfonate derivative and preparation method and application thereof
  • Novel ferulic acid sulfonate derivative and preparation method and application thereof
  • Novel ferulic acid sulfonate derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] A class of novel ferulic acid sulfonate derivatives of the present invention, the structural formula of described a class of novel ferulic acid sulfonate derivatives is as shown in formula (I):

[0023]

[0024]

[0025] Wherein, R is selected from:

[0026] The preparation method of described a class of novel ferulic acid sulfonate derivatives of the present invention, comprises the steps:

[0027] Dissolve ferulic acid in dichloromethane, add a variety of sulfonyl chlorides, stir for 60 minutes under ice bath conditions, add 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride and 1-hydroxybenzotriazole, moved to room temperature and stirred for 8 hours, thin-layer chromatography followed the reaction, filtered the precipitate after the reaction, extracted the filtrate with an extractant, washed with saturated sodium chloride solution, and distilled under reduced pressure Remove the organic solvent, use the mixed solvent of acetone and ethanol to recrys...

Embodiment 2

[0036] The difference between embodiment 2 and embodiment 1 is: the preparation method of described a class of novel ferulic acid sulfonate derivatives of the present invention, comprises the steps:

[0037] Dissolve ferulic acid in dichloromethane, add a variety of sulfonyl chlorides, stir for 30 minutes under ice bath conditions, add 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride and 1-hydroxybenzotriazole, moved to room temperature and stirred for 5 hours, followed by thin-layer chromatography. After the reaction, the precipitate was filtered, and the filtrate was extracted with an extractant, washed with saturated sodium chloride solution, and evaporated under reduced pressure. Remove the organic solvent, use the mixed solvent of acetone and ethanol to recrystallize, and prepare a new class of ferulic acid sulfonate derivatives.

[0038] The extractant is dichloromethane.

[0039] The saturated sodium chloride solution was washed 8 times.

Embodiment 3

[0041] The difference between embodiment 3 and embodiment 1 is: the preparation method of described a class of novel ferulic acid sulfonate derivatives of the present invention, comprises the steps:

[0042] Dissolve ferulic acid in dichloromethane, add a variety of sulfonyl chlorides, stir for 45 minutes under ice bath conditions, add 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride and 1-hydroxybenzotriazole, moved to room temperature and stirred for 10 hours, thin-layer chromatography followed the reaction, filtered the precipitate after the reaction, extracted the filtrate with an extractant, washed with saturated sodium chloride solution, and distilled under reduced pressure Remove the organic solvent, use the mixed solvent of acetone and ethanol to recrystallize, and prepare a new class of ferulic acid sulfonate derivatives.

[0043] The extractant is dichloromethane.

[0044] The saturated sodium chloride solution was washed 5 times.

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PUM

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Abstract

The invention discloses a novel ferulic acid sulfonate derivative and a preparation method and application thereof. A structural formula of the novel ferulic acid sulfonate derivative is as shown in aformula (I) in the specification, wherein R is selected from groups as shown in the specification. The compound has potential pharmaceutical activity, ferulic acid as the preparation raw material canbe obtained by a natural extraction method which has a positive effect on realization of resource utilization of spartina alterniflora. The obtained ferulic acid sulfonate derivative has potential pharmaceutical activity.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a new class of ferulic acid sulfonate derivatives and their preparation methods and applications. Background technique [0002] Ferulic acid, that is, 4-hydroxy 3-methoxycinnamic acid, is one of the important derivatives of cinnamic acid. Research reports have proved that it can scavenge free radicals, increase the expression of enzymes related to scavenging free radicals, and increase glutathione. Peptide sulfur transferase and quinone reductase activity, while inhibiting the activity of tyrosinase, and then actively regulate the physiological functions of the human body. At the same time, it has the effects of anti-platelet aggregation, enhancing prostaglandin activity, analgesia, and relieving vasospasm. It is the basic raw material for the production of drugs for the treatment of cardiovascular and cerebrovascular diseases and leukopenia, such as Xinxuekang and L...

Claims

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Application Information

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IPC IPC(8): C07C309/65C07C309/71C07C303/28C07C303/34C07C307/02
CPCC07C309/65C07C309/71C07C307/02C07C2601/02
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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