4-aryl coumarin compound and preparation method and application thereof

A technology of aryl coumarins and compounds, which is applied in the field of 4-aryl coumarins and their preparation, and can solve problems such as just starting

Inactive Publication Date: 2013-04-03
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

[0003] As an important category of aryl coumarins, 4-aryl coumarins have been paid more and more attention to their chemical synthesis and biological activity in recent years, but the related research is still in its infancy

Method used

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  • 4-aryl coumarin compound and preparation method and application thereof
  • 4-aryl coumarin compound and preparation method and application thereof
  • 4-aryl coumarin compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of 3,4-dimethoxyphenylacrylic acid

[0038] Add 2.08g (0.02mol) of malonic acid, 2.8g (0.017mol) of 3,4-dimethoxybenzaldehyde, 3mL of pyridine, and 0.3mL of hexahydropyridine into a 100mL double-necked reaction flask, and heat to 95°C Reflux for 3 hours, after the reaction is complete, cool for 10 minutes, add 50 mL of 10 mol / L hydrochloric acid solution, let stand for 2 hours, filter with suction, and wash the precipitate with 200 mL of water to obtain crude 3,4-dimethoxyphenylacrylic acid. Then recrystallized with absolute ethanol to obtain 3.1 g of pure 3,4-dimethoxyphenylacrylic acid, with a yield of 88.3%.

Embodiment 2

[0040]Preparation of 3-Hydroxy-4-Methoxyphenyl Acrylic Acid

[0041] Add 12.98g (0.125mol) of malonic acid, 12.65g (0.083mol) of 3-hydroxy-4-methoxybenzaldehyde, 15mL of pyridine, and 0.5mL of hexahydropyridine into a 100mL double-necked reaction flask, and heat to 95°C After reflux for 3 hours, the reaction was completed, cooled for 60 minutes, added 50 mL of 3mol / L hydrochloric acid solution, left for 10 hours, filtered with suction, and washed the solid with water to obtain crude 3-hydroxy-4-methoxyphenylacrylic acid. Then recrystallized from absolute ethanol to obtain 14.63 g of pure 3-hydroxy-4-methoxyphenylacrylic acid, with a yield of 90.6%.

Embodiment 3

[0043] Preparation of 3-Hydroxy-4-methoxyphenylpropiolic acid

[0044] Dissolve 1.94g (10mmol) of 3-hydroxy-4-methoxyphenylacrylic acid obtained in Example 2 in 30mL of absolute ethanol, add 1mL of SOCl 2 Heat to reflux for 2 hours, stop heating, concentrate the reaction solution, add water, the product precipitates, place it, and filter with suction to obtain crude ethyl 3-hydroxy-4-methoxyphenyl acrylate. Dissolve the crude ethyl 3-hydroxy-4-methoxyacrylate in 30 mL of acetic acid, add 1 mL of SOCl 2 Heat to reflux. After reacting for 2 hours, the heating was stopped, and water was added, and the product precipitated naturally. After standing overnight, the product solidified and was filtered by suction to obtain crude ethyl 3-hydroxy-4-acetoxyphenyl acrylate. Dissolve ethyl 3-hydroxy-4-acetoxyphenyl acrylate in 20 mL of dichloromethane, add 0.5 mL of Br dropwise in ice bath 2 (9.8mmol), 5min added, stirred for 3h, washed the reaction solution, spin-dried, left overnight ...

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Abstract

The invention discloses a 4-aryl coumarin compound and a preparation method and application thereof. The 4-aryl coumarin compound has a structure shown in a formula (I). The preparation method comprises the following steps: taking substituted benzaldehyde and propandioic acid as raw materials, heating under condition of existing pyridine and piperidine, and generating Perkin reaction and decarboxylic reaction to obtain a series of substituted phenylacrylic acid compounds; carrying out bromination and elimination reaction on the substituted phenylacrylic acid compounds or acetylation to protect a phenolic hydroxyl group, and then carrying out bromination and elimination reaction to obtain substituted phenylpropiolic acid compounds; and enabling the substituted phenyl propargylic acid compounds and phenolic compounds to react under the catalysis of boron trifluoride etherate and phosphorus oxychloride or trifluoroacetic acid to obtain a series of 4-aryl coumarin compounds. The compounds can be used for preparing antineoplastic medicine, anti-abnormal-angiogenesis medicine, antimicrobial medicine, antioxidation medicine and antimalarial medicine.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to a 4-aryl coumarin compound and its preparation method and application. Background technique [0002] Arylcoumarin (aryl-2H-1-benzopyran-2-one) is the basic structure of some natural products and widely exists in nature. Arylcoumarins mainly include 3-arylcoumarins and 4-arylcoumarins. Because it has a similar skeleton structure to 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;...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/16A61K31/37A61P35/00A61P39/06A61P31/04A61P33/06A61P9/00
CPCY02A50/30
Inventor 邹永孙捷张克云丁为现高蓝武玉平
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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