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A kind of furanocoumarin derivative and its preparation method

A technology of furanocoumarin and its derivatives, which is applied in the field of medicine, can solve problems that have not been reported, and achieve the effect of low loss rate and simple condensation reaction steps

Active Publication Date: 2019-01-08
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Therefore, isopsoralen and its derivatives whose furan ring is substituted by methyl have potential pharmaceutical activity, and such compounds have not been reported so far

Method used

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  • A kind of furanocoumarin derivative and its preparation method
  • A kind of furanocoumarin derivative and its preparation method
  • A kind of furanocoumarin derivative and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 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:

[0037]

[0038] Molecular formula: C 12 h 14 o 4

[0039] Chinese name: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate

[0040] English name: ethyl 3-m...

Embodiment 2

[0045] 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:

[0046]

[0047] Molecular formula: C 10 h 10 o 4

[0048] Chinese name: 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid

...

Embodiment 3

[0055] 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:

[0056]

[0057] Molecular formula: C 9 h 10 o 2

[0058] Chinese name: 3-methy...

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Abstract

The invention relates to the field of medicines and aims to provide a furan coumarin derivative and a preparation method thereof. A furan ring of the furan coumarin derivative is substituted with a methyl; the preparation method of the furan coumarin derivative comprises the following steps: taking 4-hydroxy-3-methylbenzofuran-5-carbaldehyde and weak base, uniformly dispersing in a reaction solvent a to obtain a raw material mixture, then carrying out a reaction for 1-3 hours at a temperature of 70 DEG C, filtering reaction liquid to obtain a precipitate, and washing the precipitate to obtain the furan coumarin derivative. The furan coumarin derivative provided by the invention is an isopsoralen analogue with a novel skeleton and has potential drug activity; the preparation of the compound can provide a support for the research on the activity of a furan coumarin drug; the preparation method provided by the invention is simple in step and low in loss rate.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a furanocoumarin derivative and a preparation method thereof. Background technique [0002] Furocoumarins are widely found in nature. Traditional Chinese medicines such as Angelica dahurica, Duhuo, Qianhu, Angelica, Psoralen, etc., and various medicinal plants reported abroad all contain furanocoumarins. Furocoumarins have many pharmacological activities, mainly in anti-tumor, anti-HIV, anti-oxidation, photochemical action, anti-pathogenic microorganisms, anti-inflammatory analgesia, anti-depression, and effects on drug-metabolizing enzymes. Among them, isopsoralen, an angular furanocoumarin, has strong photosensitization, sedative, antispasmodic, and hemostatic effects, and is an effective drug for treating vitiligo, alopecia areata, psoriasis, and tumor-like skin diseases. Isopsoralen has a cell proliferation-promoting effect similar to that of estrogen, and can regulate the endocrine ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/85C07D307/79C07D493/04
CPCC07D307/79C07D307/85C07D493/04
Inventor 吴军何兴瑞娄永根商志才顾海宁
Owner ZHEJIANG UNIV
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