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3,4-dihydro-4-aryl coumarin compounds as well as preparation method and application thereof

A technology of aryl coumarin and phenolic compounds, which is applied in 3 fields, can solve the problems of severe reaction conditions, low yield, and use restrictions, and achieve the effect of high yield and simple operation

Inactive Publication Date: 2010-12-08
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the existing 3,4-dihydro-4-aryl coumarin preparation methods have the disadvantages of severe reaction conditions and low yields, and these molecules are not stable under severe conditions, which makes the existing Some methods are limited in use

Method used

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  • 3,4-dihydro-4-aryl coumarin compounds as well as preparation method and application thereof
  • 3,4-dihydro-4-aryl coumarin compounds as well as preparation method and application thereof
  • 3,4-dihydro-4-aryl coumarin compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 3, the preparation of 4-dimethoxyphenylacrylic acid:

[0029] Add 2.08g (0.02mol) malonic acid, 2.8g (0.017mol) 3,4-dimethoxybenzaldehyde, 3ml (0.037mol) pyridine, 0.3ml (0.003mol) six Hydropyridine, heated to 95°C and refluxed for 3 hours, the reaction was completed, cooled for 10 minutes, added 50ml of 3mol / L hydrochloric acid solution, left for 2 hours, filtered with suction, washed with 200ml of water to obtain the crude product; the crude product was recrystallized with absolute ethanol to obtain the pure product 3.1 g of 3,4-dimethoxyphenylacrylic acid, yield 88.3%.

Embodiment 2

[0031] Preparation of 3-hydroxy-4-methoxyphenylacrylic acid:

[0032] Add 12.98g (0.125mol) malonic acid, 12.65g (0.083mol) 3-hydroxyl-4-methoxybenzaldehyde, 15ml (0.168mol) pyridine, 1.5ml (0.015mol) in a 100ml double-necked reaction flask Hexahydropyridine, heated to 95°C and refluxed for 3 hours, after the reaction was completed, cooled for 10 minutes, added 50ml of 3mol / L hydrochloric acid solution, stood for 2 hours, filtered with suction, washed the precipitate with 1000ml of water, and obtained the crude product; the crude product was recrystallized with absolute ethanol to obtain pure Product 3-hydroxy-4-methoxyphenylacrylic acid 14.63g, yield 90.6%.

Embodiment 3

[0034] Preparation of 4-(3',4'-dimethoxyphenyl)-7-hydroxyl-3,4-dihydrocoumarin:

[0035] Place a 100ml double-necked reaction flask in an ice bath, then add 2.08g (0.01mol) 3,4-dimethoxyphenylacrylic acid, 1.1g (0.01mol) resorcinol, 3g (0.02mol) tris Phosphorus oxychloride, 5.6g (0.04mol) boron trifluoride ether, stir evenly, remove the ice bath after 10min, stir at room temperature (15-30°C), TLC monitors the reaction process (developing agent: petroleum ether: ethyl acetate = 2 : 1), after 12h, the reaction was stopped, poured into ice water, extracted with ether, spin-dried to remove the ether to obtain crude product; recrystallized with acetone and water to obtain pure product 4-(3', 4'-dimethoxyphenyl )-7-hydroxy-3,4-dihydrocoumarin 1.82g, yield 60.7%.

[0036] IR: 3429(OH), 1761(CO), 1626, 1597, 1516, 1462, 1419, 1335, 1271, 1244, 1159, 1103, 1024, 991, 847 and 812cm -1

[0037] 1HNMR (400MHz, CDCl 3 )δ: 2.98(2H, m, C-3H), 3.79and 3.84(6H, 2s, 3H and 3H each, 2×OCH ...

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Abstract

The invention discloses 3,4-dihydro-4-aryl coumarin derivatives as well as a preparation method and application thereof. The preparation method comprises the following steps of: with substituted benzaldehyde and malonic acid as raw materials, heating in the presence of pyridine and piperidine and generating a Perkin reaction and a decarboxylic reaction to obtain substituted phenylacrylic acid derivatives; and then subjecting the substituted phenylacrylic acid derivatives and phenol compounds to a reaction in the presence of the catalysis of boron trifluoride diethyl ether and phosphorus oxychloride to obtain the 3,4-dihydro-4-aryl coumarin compounds. The compounds can be used for preparing medicaments for resisting tumors, abnormal vascular proliferation, bacterial and oxidation.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a 3,4-dihydro-4-aryl coumarin compound and its preparation method and application. Background technique [0002] Arylcoumarin (arylcoumarin, aryl-2H-1-benzopyran-2-one) mainly includes 3-arylcoumarin and 4-arylcoumarin, which are some natural products basic structure. Because it has a similar skeleton structure to many active natural products such as isoflavones and stilbenes, it has attracted the attention of researchers. Studies have shown that aryl coumarin compounds have a variety of beneficial physiological activities, such as anti-leukemia (Leuk.Res.2008, 32: 1914; J.Med.Chem, 2003, 46: 5437; Exp. 36:1625), antifungal (Life.Sci.2002, 71:1449; Microbiology, 2005, 151:1691), anticoagulant (Bioorg.Med.Chem.Lett, 2006, 16:257), antioxidant (Bioorg .Med.Chem, 2007, 15: 1516), antiviral (Nat.Prod.Res.2002, 17(2): 91), anti-inflammatory (Nat.Prod.Res, 2007, 21(12): 1104; Immu ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/20A61K31/37A61P35/00A61P39/06A61P31/00A61P31/04
Inventor 邹永孙捷丁为现张克云高艳明高蓝
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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