Novel ferulic acid aromatic derivative and preparation method and application thereof

A technology of ferulic acid and its derivatives, applied in the field of novel ferulic acid aromatic derivatives and its preparation

Pending Publication Date: 2019-12-13
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 type of aromatic derivatives of ferul...

Method used

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

Examples

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preparation example Construction

[0029] The preparation method of a novel ferulic acid aromatic derivative of the present invention comprises the following steps:

[0030] Dissolve ferulic acid in a mixed solution of dichloromethane and N,N-dimethylformamide, add various arylsulfonyl chlorides, stir for 60 minutes under ice bath conditions, add dicyclohexylcarbodiimide and 4-Dimethylaminopyridine, moved to room temperature and stirred for 10 h, 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, dried with saturated sodium sulfate, and reduced The organic solvent was removed by pressure distillation, and the mixed solvent of N,N-dimethylformamide and ethanol was used for recrystallization to obtain a new class of aromatic derivatives of ferulic acid.

[0031] The molar volume ratio of ferulic acid and dichloromethane is 1mmol:10mL; the volume ratio of dichloromethane and N,N-...

Embodiment 2

[0038] The difference between embodiment 2 and embodiment 1 is:

[0039] The preparation method of a novel ferulic acid aromatic derivative of the present invention comprises the following steps:

[0040] Dissolve ferulic acid in a mixed solution of dichloromethane and N,N-dimethylformamide, add various arylsulfonyl chlorides, stir for 30 minutes under ice bath conditions, add dicyclohexylcarbodiimide and 4-Dimethylaminopyridine, moved to room temperature and stirred for 12 hours, and followed the reaction by thin-layer chromatography. After the reaction was completed, the precipitate was filtered, and the filtrate was extracted with an extractant, washed with saturated sodium chloride solution, dried with saturated sodium sulfate, and reduced The organic solvent was removed by pressure distillation, and the mixed solvent of N,N-dimethylformamide and ethanol was used for recrystallization to obtain a new class of aromatic derivatives of ferulic acid.

[0041] The extractant i...

Embodiment 3

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

[0045] The preparation method of a novel ferulic acid aromatic derivative of the present invention comprises the following steps:

[0046] Dissolve ferulic acid in a mixed solution of dichloromethane and N,N-dimethylformamide, add various arylsulfonyl chlorides, stir for 50 minutes under ice bath conditions, add dicyclohexylcarbodiimide and 4-Dimethylaminopyridine, moved to room temperature and stirred for 8 hours, and followed the reaction 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, dried with saturated sodium sulfate, and reduced The organic solvent was removed by pressure distillation, and the mixed solvent of N,N-dimethylformamide and ethanol was used for recrystallization to obtain a new class of aromatic derivatives of ferulic acid. The extractant is ethyl acetate.

[004...

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Abstract

The invention discloses a novel ferulic acid aromatic derivative and a preparation method and application thereof. The structural formula of the novel ferulic acid aromatic derivative is shown as a formula (I) which is described in the specification. In the formula (I), R is described in the specification. The novel ferulic acid aromatic derivative of the invention has potential medicinal activity; and the preparation raw material, namely ferulic acid, of the derivative can be obtained by using a natural extraction method, which has positive effect on resource utilization of Spartina alterniflora Loisel.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a novel aromatic derivative of ferulic acid and its preparation method and application. Background technique [0002] Ferulic acid is an important class of cinnamic acid derivatives, which has a wide range of applications in regulating human body functions. Studies have shown that it can promote the expression of enzymes related to scavenging free radicals, activate glutathione sulfur transferase and quinone reductase, and at the same time inhibit the activity of tyrosinase, and finally achieve scavenging free radicals. It also has analgesic effect, the main mechanism is anti-platelet aggregation, enhancing prostaglandin activity, relieving vasospasm, etc. It is the basic raw material for the production of drugs for the treatment of cardiovascular and cerebrovascular diseases and leukopenia. Due to the pollution problems caused by industrial production, more and more...

Claims

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Application Information

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IPC IPC(8): C07C309/75C07C309/68C07C323/66C07C309/76C07C309/73C07D333/34C07C303/28C07C319/20
CPCC07C309/75C07C309/68C07C323/66C07C309/76C07C309/73C07D333/34
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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