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Preparation method of drug intermediate 1,3-dicyclohexyl barbituric acid for inhibiting angiogenesis, tumorigenesis and proliferative diseases

A technology for dicyclohexylbarbituric acid and proliferative diseases, applied in the fields of organic chemistry and drug synthesis, can solve problems such as reversible loss of female fertility, and achieve the effects of high product yield, easy operation and simple process

Inactive Publication Date: 2012-05-02
姜树林
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The only clear adverse side effect currently identified for anti-angiogenic strategies is the reversible loss of female fertility

Method used

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  • Preparation method of drug intermediate 1,3-dicyclohexyl barbituric acid for inhibiting angiogenesis, tumorigenesis and proliferative diseases
  • Preparation method of drug intermediate 1,3-dicyclohexyl barbituric acid for inhibiting angiogenesis, tumorigenesis and proliferative diseases

Examples

Experimental program
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Effect test

Embodiment 1

[0021] In a three-necked flask, add 150.0ml of glacial acetic acid, 65.0g of N'N-dicyclohexylurea and 33.0g of malonic acid, raise the temperature, add 120ml of acetic anhydride dropwise at 80°C, keep the temperature for 4 hours, and distill under reduced pressure. Add 500ml of absolute ethanol, reflux, cool to 0-5°C, stir and crystallize, and filter to obtain 75.0g of product with a content of more than 99.5%.

Embodiment 2

[0023] In a three-necked flask, add 150.0ml of glacial acetic acid, 65.0g of N'N-dicyclohexylurea and 33.0g of malonic acid, raise the temperature, add 120ml of acetic anhydride dropwise at 100°C, keep the temperature for 4 hours, and distill under reduced pressure. Add 500ml of absolute ethanol, reflux, cool to 0-5°C, stir and crystallize, and filter to obtain 78.0g of product with a content of more than 99.5%.

[0024]

Embodiment 3

[0026] Add 150.0ml of glacial acetic acid, 65.0g of N'N-dicyclohexyl urea and 33.0g of malonic acid into a three-necked flask, raise the temperature, add 120ml of acetic anhydride dropwise, keep the temperature for 4 hours, distill under reduced pressure, and add 100.0ml Water and 60.0ml concentrated hydrochloric acid were heated to reflux, cooled and filtered to obtain 59.0g with a content of more than 99.0%.

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Abstract

The invention discloses a preparation method of a drug intermediate, namely 1,3-dicyclohexyl barbituric acid, for inhibiting angiogenesis, tumorigenesis and proliferative diseases. The preparation method comprises the step of: under the conditions that acetic acid serves as a solvent and acetic anhydride serves as a dehydrating agent, reacting N,N'-dicyclohexylurea (DCU) with malonic acid to generate the 1,3-dicyclohexyl barbituric acid. The preparation method is simple in process, easy to operate, and high in product yield; and by adoption of the preparation method, the purity of the 1,3-dicyclohexyl barbituric acid is more than 99.5 percent.

Description

technical field [0001] The invention relates to a method for synthesizing a drug intermediate 1,3-dicyclohexylbarbituric acid for inhibiting angiogenesis, tumorigenesis and proliferative diseases, and belongs to the technical field of organic chemistry and drug synthesis. Background technique [0002] 1,3-Dicyclohexylbarbituric acid is a key intermediate of barbituric acid drugs that inhibit angiogenesis, tumorigenesis and proliferation diseases. Its chemical structural formula is: [0003] [0004] Chemical structure name: 1,3-dicyclohexyl-pyrimidine-2,4,6(1H,3H,5H)-trione, molecular formula is C 16 h 24 N 2 o 3 , with a molecular weight of 292.37. The present invention relates to the field of antiproliferative compounds and more particularly to active compounds that inhibit the activity of HIF-1 (eg the interaction between HIF-la and p300) and thus inhibit angiogenesis, tumorigenesis and proliferative diseases into cancer. Several cell lines used for demonstration ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/62
Inventor 王德峰王炳才祝海峰朱小飞俞健钧
Owner 姜树林
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