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Substituted furan isoflavone derivative and preparation method thereof

A technology of furan isoflavones and derivatives, which is applied in the field of medicinal chemistry, can solve problems that have not been reported, and achieve the effect of simple steps and low loss rate

Active Publication Date: 2017-01-18
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Therefore, the furan isoflavones and their derivatives with the furan ring substituted by methyl have potential pharmaceutical activity, and such compounds have not been reported so far

Method used

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  • Substituted furan isoflavone derivative and preparation method thereof
  • Substituted furan isoflavone derivative and preparation method thereof
  • Substituted furan isoflavone derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Disperse 1,3-cyclohexanedione and potassium hydroxide uniformly in water, stir at room temperature for 5 minutes, add methanol solution of ethyl chloroacetoacetate, then stir the system at room temperature for 5 days, and then use 4N Acidify with hydrochloric acid, filter the acidified reaction solution, and the obtained solid is the product: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate. In this step, the molar ratio of 1,3-cyclohexanedione to potassium hydroxide and ethyl chloroacetoacetate is 1:1:1, and the feeding amount of 1,3-cyclohexanedione corresponding to every milliliter of water is 0.1g , the feeding amount of ethyl chloroacetoacetate corresponding to every milliliter of methanol is 0.2g. The yield for this step was 65%. The structure of the resulting product is:

[0036]

[0037] Molecular formula: C 12 h 14 o 4

[0038] Chinese name: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate

[0039] English name: ethyl 3-m...

Embodiment 2

[0044]Dissolve ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate and potassium hydroxide in a mixed solvent of methanol and water, and stir the system at room temperature after dissolution Reaction 5h. Then adjust the pH of the reaction solution to 1 with 6N hydrochloric acid, filter the reaction solution, and filter the obtained solid as the product: 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2- formic acid. The mixed solvent used in this step is methanol and water at a ratio of 2.5:1. The feeding amount of ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate per milliliter of mixed solvent is 0.2 g. In this step, the molar ratio of ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate to potassium hydroxide was 1:6. The yield for this step was 90%. The structure of the resulting product is:

[0045]

[0046] Molecular formula: C 10 h 10 o 4

[0047] Chinese name: 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid

...

Embodiment 3

[0053] Disperse 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid evenly in diethylene glycol, add copper powder and pyridine, then heat the system to 175°C, Keep stirring for 10h. Cool the system to room temperature, add ice water, and acidify with 4N hydrochloric acid, extract the acidified reaction solution with petroleum ether three times, wash the combined extract with water once, then dry the extract with anhydrous sodium sulfate, and spin dry. The obtained solid is the product: 3-methyl-6,7-dihydrobenzofuran-4-(5H)-one. In this step, the feeding amount of 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid per milliliter of diethylene glycol is 0.1 g. In this step, the molar ratio of 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid to copper powder and pyridine is 1:1:2. The yield for this step was 85%. The structure of the resulting product is:

[0054]

[0055] Molecular formula: C 9 h 10 o 2

[0056] Chinese name: 3-methy...

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Abstract

The invention relates to the field of medicinal chemistry, aims to provide a substituted furan isoflavone derivative and a preparation method thereof. The substituted furan isoflavone derivative has a structure represented by the formula (I), wherein R1 and R2 are separately independently selected from the group consisting of a hydrogen atom, methyl, methoxyl or halogen. The product is a natural furan isoflavone analogue having a novel skeleton, and has potential pharmaceutical activity; the preparation of the compound can provide a support for research of the pharmaceutical activity of furan isoflavones; the preparation method has the advantages of simple steps and low loss rate and has great significance for industrialized production.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, more specifically, to a substituted furan isoflavone derivative and a preparation method thereof. Background technique [0002] Isoflavones have preventive and even curative uses for cardiovascular diseases, osteoporosis and menopausal syndrome. Isoflavone resources are very limited in nature, and soybean is the only food resource that contains isoflavones and its content is nutritionally meaningful. Therefore, it is of great significance to develop new synthetic routes of isoflavones in organic synthesis. [0003] Methyl-substituted furan ring structures widely exist in natural products and have diverse biological activities, such as tanshinone can treat cardiovascular diseases, furofromane has phytoallelopathy, sesquiterpenoid cacalol has anti-hyperglycemic and Antibacterial effect. [0004] Therefore, the furan isoflavones and their derivatives with the furan ring substituted by a methyl g...

Claims

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Application Information

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IPC IPC(8): C07D493/04
CPCC07D493/04
Inventor 吴军何兴瑞娄永根商志才顾海宁
Owner ZHEJIANG UNIV
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