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P-coumaric acid aromatic derivative and preparation method and application thereof

A technology of p-coumaric acid and derivatives, applied in the preparation of sulfonates, organic chemistry, etc.

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 class of aromatic derivatives of p-coumaric acid for resource utilization of Spartina and its preparation method and application

Method used

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  • P-coumaric acid aromatic derivative and preparation method and application thereof
  • P-coumaric acid aromatic derivative and preparation method and application thereof
  • P-coumaric acid aromatic derivative and preparation method and application thereof

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Effect test

Embodiment 1

[0026] A class of p-coumaric acid aromatic derivatives of the present invention, the structural formula of the described class of p-coumaric acid aromatic derivatives is shown in formula (I):

[0027]

[0028] Wherein, R is selected from:

[0029]

[0030] The synthesis process of a class of p-coumaric acid aromatic derivatives of the present invention has the following general formula:

[0031]

[0032] Wherein, R is selected from:

[0033] The preparation method of a class of p-coumaric acid aromatic derivatives described in the present invention comprises the following steps:

[0034] Dissolve p-coumaric 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 8 hours, followed by thin-layer chromatography. After the reaction, the precipitate was filtered, and the...

Embodiment 2

[0042] The difference between embodiment 2 and embodiment 1 is: the preparation method of a class of p-coumaric acid aromatic derivatives of the present invention, comprises the following steps:

[0043] Dissolve p-coumaric 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 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 dried with saturated sodium sulfate. The organic solvent was distilled off under reduced pressure, and recrystallized using a mixed solvent of N,N-dimethylformamide and ethanol to obtain a class of aromatic derivatives of p-coumaric acid.

[0044] The extractant is ethyl acetate. The saturated sodium chloride ...

Embodiment 3

[0046] The difference between embodiment 3 and embodiment 1 is:

[0047] The preparation method of a class of p-coumaric acid aromatic derivatives described in the present invention comprises the following steps:

[0048] Dissolve p-coumaric 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 6 hours, and followed the reaction by thin layer chromatography. After the reaction, the precipitate was filtered, and the filtrate was extracted with ethyl acetate, washed with saturated sodium chloride solution, and dried with saturated sodium sulfate. , the organic solvent was distilled off under reduced pressure, and recrystallized using a mixed solvent of N,N-dimethylformamide and ethanol to obtain a class of aromatic derivatives of p-coumaric acid.

[0049] The saturated sodium chlor...

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Abstract

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

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a class of p-coumaric acid aromatic derivatives and a preparation method and application thereof. Background technique [0002] Hydroxycinnamic acid compounds are widely used in medicinal chemistry, among which, p-coumaric acid is a kind of important drug prodrug molecule that has been reported, and has activities such as anti-oxidation, antibacterial, and treatment of cardiovascular diseases. The development of p-coumaric acid drugs is also of great significance to the treatment of hyperuricemia and gout. Among the production methods of p-coumaric acid, the chemical synthesis method is likely to cause pollution to the ecological environment, while the biotransformation method is limited by the type of fermentation raw materials and cannot be used as a stable production source. Therefore, the natural extraction method is the most environmentally friendly and quality-f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/73C07C309/67C07C309/75C07C309/74C07C303/28C07D333/34
CPCC07C309/67C07C309/73C07C309/74C07C309/75C07D333/34
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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