Quinoid chalcone compound with methyl group at A ring, and preparation method and anti-inflammatory activity thereof

A technology of trihydroxychalcones and compounds, applied in the field of medicine, can solve problems such as easy destruction, unstable chemical properties, and limited development and utilization

Active Publication Date: 2015-11-25
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the physical and chemical properties of hydroxysafflower yellow A are unstable, and it is easily destroyed and difficult to preserve under light, heat, acid-base conditions, which limits its further development and utilization.
[0004] At present, the synthesis and pharmacological research on quinone chalcones is still not in-depth. In order to effectively explain the mechanism of traditional Chinese medicine and provide theoretical basis and practical experience for finding more active anti-inflammatory drugs, we synthesized a Quinochalcones with a methyl group in the A-like ring and evaluation of their anti-inflammatory activity

Method used

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  • Quinoid chalcone compound with methyl group at A ring, and preparation method and anti-inflammatory activity thereof
  • Quinoid chalcone compound with methyl group at A ring, and preparation method and anti-inflammatory activity thereof
  • Quinoid chalcone compound with methyl group at A ring, and preparation method and anti-inflammatory activity thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] The synthetic method of compound 1, comprises the following steps:

[0061] (1) Synthesis of 2-hydroxy-4,6-dimethoxymethoxyacetophenone

[0062] Add 1g of 2,4,6-trihydroxyacetophenone to anhydrous acetone, stir to dissolve, take 6.1g of potassium carbonate, add to acetone; after 15 minutes, take 1.13ml of chloromethyl methyl ether, add to acetone middle. After stirring and reacting for 5 hours, filter and dry the filtrate, and finally use a mixed solvent of petroleum ether / ethyl acetate with a volume ratio of 10:1, and perform silica gel column chromatography to obtain: 2.4g yellow oily solid 2-hydroxy-4,6-dimethyl Oxymethoxyacetophenone, productive rate is 79%; This process takes place following reaction:

[0063]

[0064] The structural characterization data of the product are: 1 HNMR (acetone-d 6 ,300MHz)δ2.643(3H,s,CH 3 ),3.443(3H,s,OCH 3 ),3.524(3H,s,OCH 3 ),5.242(2H,s,OCH 2 O),5.356(2H,s,OCH 2 O),6.195(1H,d,J=2.1Hz,H-3),6.292(1H,d,J=2.1Hz,H-5),13.738(1...

Embodiment 2

[0078] The synthetic method of compound 2, comprises the following steps:

[0079] (1) Synthesis of 2-hydroxy-4,6-dimethoxymethoxyacetophenone

[0080] Add 1g of 2,4,6-trihydroxyacetophenone to anhydrous acetone, stir to dissolve, take 6.1g of potassium carbonate, add to acetone; after 15 minutes, take 1.13ml of chloromethyl methyl ether, add to acetone middle. After stirring and reacting for 5 hours, filter and dry the filtrate, and finally use a mixed solvent of petroleum ether / ethyl acetate with a volume ratio of 10:1, and perform silica gel column chromatography to obtain: 2.4g yellow oil 2-hydroxy-4,6-dimethyl Oxymethoxyacetophenone, productive rate is 79%; This process takes place following reaction:

[0081]

[0082] The structural characterization data of the product are: 1 HNMR (acetone-d 6 ,300MHz)δ2.643(3H,s,CH 3 ),3.443(3H,s,OCH 3 ),3.524(3H,s,OCH 3 ),5.242(2H,s,OCH 2 O),5.356(2H,s,OCH 2 O),6.195(1H,d,J=2.1Hz,H-3),6.292(1H,d,J=2.1Hz,H-5),13.738(1H,s,OH)...

Embodiment 3

[0096] The synthetic method of compound 3 comprises the following steps:

[0097] (1) Synthesis of 2-hydroxy-4,6-dimethoxymethoxyacetophenone

[0098] Add 1g of 2,4,6-trihydroxyacetophenone to anhydrous acetone, stir to dissolve, take 6.1g of potassium carbonate, add to acetone; after 15 minutes, take 1.13ml of chloromethyl methyl ether, add to acetone middle. After stirring and reacting for 5 hours, filter and dry the filtrate, and finally use a mixed solvent of petroleum ether / ethyl acetate with a volume ratio of 10:1, and perform silica gel column chromatography to obtain: 2.4g yellow oil 2-hydroxy-4,6-dimethyl Oxymethoxyacetophenone, productive rate is 79%; This process takes place following reaction:

[0099]

[0100] The structural characterization data of the product are: 1 HNMR (acetone-d 6 ,300MHz)δ2.643(3H,s,CH 3 ),3.443(3H,s,OCH 3 ),3.524(3H,s,OCH 3 ),5.242(2H,s,OCH 2 O),5.356(2H,s,OCH 2 O),6.195(1H,d,J=2.1Hz,H-3),6.292(1H,d,J=2.1Hz,H-5),13.738(1H,s,OH)....

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Abstract

The invention discloses a quinoid chalcone compound with a methyl group at an A ring, and a preparation method and anti-inflammatory activity thereof. The compound has a structure as shown in a general formula (I) which is described in the specification. The preparation method comprises the following steps: (1) synthesizing 2-hydroxy-4,6-dimethoxyacetophenone; (2) synthesizing 2'-hydroxy-4',6'-dimethoxychalcone derivative; (3) synthesizing 2',4',6'-trihydroxy chalcone derivative; and (4) synthesizing the quinoid chalcone compound with a methyl group at the A ring. The compound is simple to prepare and has obvious anti-inflammatory action.

Description

technical field [0001] The invention relates to the technical field of medicine, a class of compounds with a quinoidal chalcone structure with a methyl group in the A ring, a preparation method, a pharmaceutical composition containing them and their application in anti-inflammation. Background technique [0002] Vascular endothelial injury refers to the direct or indirect damage of vascular endothelial cells due to physical, chemical, radiation, cytokine and bacterial damage. After the vascular endothelium is damaged, the damaged part not only loses the function of the endothelial barrier, but also produces a variety of cytokines, which strongly stimulate and induce the production of a large amount of inducible nitric oxide synthase (iNOS). iNOS expresses rapidly and catalyzes the production of 1000 times the normal physiological amount of NO, a large amount of NO produced combines with oxygen molecules or peroxides to form oxygen free radical ROS (OONO - ) or RNS (NO 2 , ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/747C07C49/753C07C45/00C07C45/61A61K31/122A61P29/00A61P25/02A61P19/02A61P19/04A61P9/14A61P9/00A61P9/10A23L1/29A23L33/00
Inventor 张培成侯琦陈钟林明宝杨桠楠袁绍鹏冯子明白金叶姜建双
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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