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A quinone-type chalcone compound with isopentenyl group, preparation method and anti-inflammatory activity

A technology of prenyl and di-prenyl rings, applied in the field of medicine, can solve the problems of limited development and utilization, insufficient synthesis and pharmacological research of quinone chalcones, and easy damage

Active Publication Date: 2019-04-09
稷冲(北京)医药有限公司
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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 studies related to quinone chalcones are not yet in-depth. In order to effectively explain the mechanism of action of traditional Chinese medicine and provide theoretical basis and practical experience for finding more active anti-inflammatory drugs, we synthesized a class of A Quinochalcones with a prenyl group in the ring and their anti-inflammatory activity evaluated

Method used

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  • A quinone-type chalcone compound with isopentenyl group, preparation method and anti-inflammatory activity
  • A quinone-type chalcone compound with isopentenyl group, preparation method and anti-inflammatory activity
  • A quinone-type chalcone compound with isopentenyl group, preparation method and anti-inflammatory activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0061] (1) Synthesis of 3,5-dihydroxy-2-acetyl-6,6-diisopentenylcyclohexa-2,4-dienone

[0062] Add 1g of 2,4,6-trihydroxyacetophenone and 0.68g of potassium hydroxide to 10ml of water, stir in an ice-water bath to dissolve, take 1.37ml of bromoisoamylene, add it to the aqueous solution; after 60 minutes, adjust with dilute hydrochloric acid PH to 3, then extracted with ethyl acetate, washed the organic phase, dried, and finally used petroleum ether / ethyl acetate mixed solvent volume ratio 10:1, silica gel column chromatography to obtain 0.8g yellow oil 3,5-di Hydroxy-2-acetyl-6,6-diisopentenylcyclohexa-2,4-dienone in 44% yield; the following reactions occurred in the process:

[0063]

[0064] The structural characterization data of the product are: 1 H NMR (DMSO-d 6 ,300MHz)δ1.641(12H,s,4×CH 3 ),2.566(5H,m,-CH 2 CH=,-CH 3 CO),2.660(2H,m,-CH 2 CH=),4.894(2H,t,J=7.5Hz,=CHCH 2 ),5.661(1H,s,H-4...

Embodiment 2

[0082] The synthetic method of compound 2, comprises the following steps:

[0083] (1) Synthesis of 3,5-dihydroxy-2-acetyl-6,6-diisopentenylcyclohexa-2,4-dienone

[0084] Add 1g of 2,4,6-trihydroxyacetophenone and 0.68g of potassium hydroxide to 10ml of water, stir in an ice-water bath to dissolve, take 1.37ml of bromoprenyl, add it to the aqueous solution; after 60 minutes, wash with dilute hydrochloric acid Adjust the pH to 3, then extract with ethyl acetate, wash and dry the organic phase, 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 0.8 g of yellow oil 3,5- Dihydroxy-2-acetyl-6,6-diisopentenylcyclohexa-2,4-dienone in 44% yield; the following reactions occurred in the process:

[0085]

[0086] The structural characterization data of the product are: 1 H NMR (DMSO-d 6 ,300MHz)δ1.641(12H,s,4×CH 3 ),2.566(5H,m,-CH 2 CH=,-CH 3 CO),2.660(2H,m,-CH 2 CH=),4.894(2H,t,J...

Embodiment 3

[0104] The synthetic method of compound 3 comprises the following steps:

[0105] (1) Synthesis of 3,5-dihydroxy-2-acetyl-6,6-diisopentenylcyclohexa-2,4-dienone

[0106] Add 1g of 2,4,6-trihydroxyacetophenone and 0.68g of potassium hydroxide to 10ml of water, stir in an ice-water bath to dissolve, take 1.37ml of bromoprenyl, add it to the aqueous solution; after 60 minutes, wash with dilute hydrochloric acid Adjust the pH to 3, then extract with ethyl acetate, wash and dry the organic phase, 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 0.8 g of yellow oil 3,5- Dihydroxy-2-acetyl-6,6-diisopentenylcyclohexa-2,4-dienone in 44% yield; the following reactions occurred in the process:

[0107]

[0108] The structural characterization data of the product are: 1 H NMR (DMSO-d 6 ,300MHz)δ1.641(12H,s,4×CH 3 ),2.566(5H,m,-CH 2 CH=,-CH 3 CO),2.660(2H,m,-CH 2 CH=),4.894(2H,t,J=...

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Abstract

The invention discloses a quinoid chalcone compound with an isopentenyl 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 3,5-dihydroxy-2-acetyl-6,6-diisopentenylcyclohexyl-2,4-dienone; (2) synthesizing 3-hydroxy-5-methoxy-2-acetyl-6,6-diisopentenylcyclohexyl-2,4-dienone; (3) synthesizing a methoxy group protected quinoid chalcone compound with the isopentenyl group at the A ring; and (4) synthesizing the quinoid chalcone compound with the isopentenyl 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 having a prenyl 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 Patents(China)
IPC IPC(8): C07C49/747C07C49/753C07C45/61A61K31/122A61P29/00A61P19/02A61P19/04A61P25/00A61P9/00A61P9/10A23L33/10A23L33/00
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 稷冲(北京)医药有限公司
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