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5-hydroxy coumarin and pyranoid type coumarin compounds, synthesizing method and use

A technology of hydroxycoumarins and coumarins, which is applied in the directions of active ingredients of heterocyclic compounds, medical preparations containing active ingredients, and organic chemistry, can solve problems such as liver poisoning, achieve high yield, mature method, The effect of high therapeutic factor

Inactive Publication Date: 2009-08-05
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some naturally occurring coumarins have certain effects in anticancer, but are often accompanied by hepatotoxicity

Method used

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  • 5-hydroxy coumarin and pyranoid type coumarin compounds, synthesizing method and use
  • 5-hydroxy coumarin and pyranoid type coumarin compounds, synthesizing method and use
  • 5-hydroxy coumarin and pyranoid type coumarin compounds, synthesizing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 Preparation of Compound 1

[0030] Add 0.52 g of 5-iodo-1,3-benzenediol, 0.28 g of ethyl acetoacetate, silicon sulfonic acid (SO 2 -OSO 3 H) 0.9 g (equivalent to 2.3 mmol H + ), and added 10 ml of dichloromethane, and refluxed for 6 hours. After the reaction was complete, dissolve with hot ethanol and filter to remove silicon sulfonic acid, recrystallize from ethanol to obtain white crystal compound 1, yield 94.1%, melting point: 262 ℃ of decomposition, mass spectrum (APCI-MS): 302.6 (calculated value: 302.07 ).

Embodiment 2

[0031] Example 2 Preparation of Compound 2

[0032] Add 1.18 grams of 5-iodo-1,3-benzenediol, 0.79 grams of ethyl butyryl acetate, silicon sulfonic acid (SO 2 -OSO 3 H) 1.9 g (equivalent to 4.8 mmol H + ), and added 10 ml of dichloromethane, and refluxed for 6 hours. After the reaction is complete, dissolve with hot ethanol and filter to remove silicon sulfonic acid, recrystallize from ethanol to obtain white crystal compound 2, yield: 90.2%, melting point: 232-233 ° C, mass spectrum (APCI-MS): 330.7 (calculated value: 330.7).

Embodiment 3

[0033] Example 3 Preparation of Compound 3

[0034] Add 1.18 grams of 5-iodo-1,3-benzenediol, 0.96 grams of ethyl benzoylacetate, silicon sulfonic acid (SO 2 -OSO 3 H) 1.9 g (equivalent to 4.8 mmol H + ), and added 10 ml of dichloromethane, and refluxed for 8 hours. After the reaction is complete, dissolve with hot ethanol and filter to remove silicon sulfonic acid, recrystallize from ethanol to obtain light yellow crystal compound 3, yield: 89.0%, melting point: 240-241 ° C, mass spectrum (ESI-MS): 362.8 [M-H] + (calculated value: 364.13).

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Abstract

The invention relates to a compound of 5-hydroxycoumarin and pyranocoumarin and synthesis and application thereof. The compound has a structural formula I or II; during preparation, according to the mol portion, under the catalytic action of 2 to 6 portions of SO2-OSO3H(silicon sulfonic acid), 1 to 3 portions of 5-iodine-1 and 3-dihydroxyhenzene and 1 to 3 portions of RCOCH2COOCH2CH3 are condensed to obtain the compound of which the structural formula is iodo-5-hydroxycoumarin; 1 to 4 portions of compound of iodo-5-hydroxycoumarin and 2 to 8 portions of 3-methyl-2-crotonaldehyde or 3-chloro-3-methylbutyne are reacted to generate a compound of iodo-pyranocoumarin; and finally, by coupled reaction, the coumarin compound with the structural formula I or II is generated. The IC50 value of the compound on breast cancer cells MCF-7 reaches 3.3 to 18.3, so that the compound can strongly inhibit the breast cancer cells MCF-7.

Description

technical field [0001] The invention relates to 5-hydroxycoumarin and pyranocoumarin derivatives. These compounds have inhibitory effects on MCF-7 cells, some of which have obvious inhibitory effects, and can be used to prepare lead substances of breast cancer drugs . technical background [0002] Coumarin compounds are widely distributed in plants, and the coumarin ring system appears in natural products (for example, Calanolide A, a natural product from a variety of tropical plants of the genus Americano, is concentrated around a phloroglucinol core The coumarin, chromane and benzopyran ring system, which is a potent inhibitor of human immunodeficiency virus-1 reverse transcriptase) usually have special pharmacological properties, which greatly inspired chemists and medicinal chemists exploring the interest of natural coumarins or their synthetic analogues as pharmaceuticals. Many derivatives synthesized based on coumarin ring system, such as furanocoumarin, pyranocoumar...

Claims

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Application Information

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IPC IPC(8): C07D311/16C07D493/04C07D409/04A61K31/37A61K31/381A61K31/385A61P35/00
Inventor 曾和平毛魏魏王婷婷
Owner SOUTH CHINA UNIV OF TECH
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