1,2-diaryl-2-propenyl-1-ketone compounds and use thereof

A ketone compound, disubstituted technology, applied in the field of medicine, can solve the problem that the research on anti-tumor activity has not yet been reported, etc.

Inactive Publication Date: 2013-07-03
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 1,2-disubstituted aryl-2-propen-1-one compounds have not been reported as antitumor activity

Method used

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  • 1,2-diaryl-2-propenyl-1-ketone compounds and use thereof
  • 1,2-diaryl-2-propenyl-1-ketone compounds and use thereof
  • 1,2-diaryl-2-propenyl-1-ketone compounds and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0095] Example 1: Preparation of 1-(3,4,5-trimethoxyphenyl)-2-(4-methoxyphenyl)-2-propen-1-one (compound 1)

[0096] 1-(3,4,5-trimethoxyphenyl)-2-(4-methoxyphenyl)ethanone (0.1 g, 0.316 mmol) was dissolved in methanol, and 0.1 equivalent of piperidine ( 2.69 mg, 0.0316 mmol), 0.16 equivalents of glacial acetic acid (3.062 mg, 0.051 mmol) and 4.2 equivalents of paraformaldehyde (39.8 mg, 1.327 mmol), react at 50°C for 2 hours. After the reaction was completed, excess paraformaldehyde in the reaction solution was filtered off, the solvent was evaporated to dryness under reduced pressure, and then extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated by a rotary evaporator, and the product was obtained by separation and purification by column chromatography. Yield 92.0%; The structural formula of compound 1, 1 H-NMR and MS data are listed in Table-1 below.

Embodiment 2

[0097] Example 2: Preparation of 1-(3,4,5-trimethoxyphenyl)-2-(3,4-dimethoxyphenyl)-2-propen-1-one (compound 2)

[0098] Except using corresponding raw materials, compound 2 is prepared in the same manner as in Example 1, and the yield is 85.2%; the structural formula of compound 2, 1 H-NMR and MS data are listed in Table-1 below.

Embodiment 3

[0099] Example 3: Preparation of 1-(3,4,5-trimethoxyphenyl)-2-(3-methoxyphenyl)-2-propen-1-one (compound 3)

[0100] Except using corresponding raw materials, compound 3 is prepared in the same manner as in Example 1, and the yield is 88.5%; the structural formula of compound 3, 1 H-NMR and MS data are listed in Table-1 below.

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Abstract

The invention belongs to the technical field of medicines, relates to 1,2-diaryl-2-propenyl-1-ketone compounds and use thereof, and particularly relates to the compounds and application thereof as a tumor cell proliferation inhibitor and a tumor vascular disrupting agent in field of preparation of anti-cancer medicines. The compounds of the present invention can be represented by a structural formula in the specification, wherein R1-R8 are defined as the specification.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a 1,2-disubstituted aryl-2-propen-1-one compound and its application, specifically, to the compound and its use as a tumor cell proliferation inhibitor and tumor Application of the vascular disruptor in the preparation of antitumor drugs. Background technique [0002] Malignant tumors are serious diseases that threaten human health and life. Finding and discovering new drugs for the treatment and prevention of tumors is a major issue at present. [0003] Combretastatin A-4 (CA-4) is a cis-stilbene natural product isolated from South African willow, and its chemical name is ( Z )-2-methoxy-5-(3,4,5-trimethoxystyryl)phenol. CA-4 is an inhibitor of tubulin polymerization, which exhibits strong anti-tumor cell proliferation activity. Its prodrug CA-4 phosphate (CA-4P) has entered the phase III clinical research stage in the United States. There have been many reports on the design ...

Claims

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Application Information

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IPC IPC(8): C07C49/84C07C45/61A61K31/12A61P35/00
Inventor 张为革倪佳吴英良沈杞容孙俊齐欢乔佛晓关奇边圣杰
Owner SHENYANG PHARMA UNIVERSITY
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