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Diaryl pyrazole compound, and preparation method and purpose thereof

A technology for diarylpyrazoles and compounds, applied in the field of medicine, can solve the problems of insufficient activity, complex synthesis, high toxicity and the like

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

There have been a lot of reports on the design and synthesis of new anti-tumor active compounds using CA-4 as the lead compound, but most CA-4 analogs have shortcomings such as insufficient activity, high toxicity, or relatively complicated synthesis.

Method used

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  • Diaryl pyrazole compound, and preparation method and purpose thereof
  • Diaryl pyrazole compound, and preparation method and purpose thereof
  • Diaryl pyrazole compound, and preparation method and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0189] Example 1: Preparation of 3-(3,4,5-trimethoxyphenyl)-4-(4-methoxyphenyl)-pyrazole (compound 1)

[0190] Dissolve 3-(3,4,5-trimethoxyphenyl)-4-(4-methoxyphenyl)-2-methylene ethyl ketone in methanol, add 25 equivalents of triethylamine and 5 The equivalent of semicarbazide hydrochloride was refluxed for 6 hours. After the reaction is completed, add 2 equivalents of 20% sodium hydroxide aqueous solution, and continue to reflux for 6 hours. After the reaction, the methanol was evaporated 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 under reduced pressure, and the compound 1 was separated and purified by column chromatography, with a yield of 65%; the structural formula of compound 1, 1 H-NMR and MS data are listed in Table-1 below.

Embodiment 2

[0191] Example 2: Preparation of 3-(3,4,5-trimethoxyphenyl)-4-(3-methoxyphenyl)-pyrazole (compound 2)

[0192] Except for using the corresponding raw materials, compound 2 was prepared by the same method as in Example 1, with a yield of 65.5%; the structural formula of compound 2, 1 H-NMR and MS data are listed in Table-1 below.

Embodiment 3

[0193] Example 3: Preparation of 3-(3,4,5-trimethoxyphenyl)-4-(3,4-dimethoxyphenyl)-pyrazole (Compound 3)

[0194] Except for using the corresponding raw materials, compound 3 was prepared by the same method as in Example 1, with a yield of 55.3%; 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, and relates to a diaryl pyrazole compound, and a preparation method and a purpose thereof. Specifically, the invention relates to the compound and the compound as a tumor cell proliferation inhibitor in preparing antitumor medicines. The compound has a structural formula represented as the following, wherein R1-R8 and X are defined as in the specifications.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a diarylpyrazole compound and its preparation method and application, specifically, to the compound and its application as a tumor cell proliferation inhibitor in the preparation of antitumor drugs. Background technique [0002] Malignant tumor is a serious disease that threatens human health and life, and it is the leading cause of death in China. Searching for 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 o...

Claims

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Application Information

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IPC IPC(8): C07D231/12A61K31/415A61K31/454A61P35/00
Inventor 张为革倪佳吴英良沈杞容孙俊齐欢乔佛晓张云然边圣杰
Owner SHENYANG PHARMA UNIVERSITY
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