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3-methyl-1,5-diaryl pyrazole compound, preparation method and application thereof

A compound, methoxyphenyl technology, applied in the field of medicine, can solve the problem that anti-tumor active compounds have not yet been reported, etc.

Active Publication Date: 2015-10-14
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] It should be pointed out that the research on 3-methyl-1,5-diarylpyrazole compounds as anti-tumor active compounds has not been reported yet.

Method used

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  • 3-methyl-1,5-diaryl pyrazole compound, preparation method and application thereof
  • 3-methyl-1,5-diaryl pyrazole compound, preparation method and application thereof
  • 3-methyl-1,5-diaryl pyrazole compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0117] Example 1: Preparation of 5-phenyl-3-methyl-1-(3,4,5-trimethoxyphenyl)-1H-pyrazole (compound 1)

[0118] 3,4,5-trimethoxyphenylhydrazine hydrochloride (0.14g, 0.62mmol), anhydrous sodium acetate (0.05g, 0.62mmol) and 1-phenylbutan-1,3-dione (0.10g ,0.62mmol) into 30mL ethanol, heated to 78°C for 1 hour reaction; after the reaction, the organic solvent was evaporated under reduced pressure, water was added to the residue, the aqueous solution was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate; The organic solvent was evaporated under reduced pressure, and compound 1 was obtained by separation and purification by column chromatography with a yield of 70.3%; 1 H-NMR (400MHz, CDCl 3 ):δ2.41(3H,s),3.66(6H,s),3.83(3H,s),6.32(1H,s),6.50(2H,s),7.25(2H,m),7.31(3H, m);MS(ESI):[M+H] + =325.1,[2M+H] + =649.3,[2M+Na] + =671.3.

Embodiment 2

[0119] Example 2: Preparation of 5-(4-fluorophenyl)-3-methyl-1-(3,4,5-trimethoxyphenyl)-1H-pyrazole (compound 2)

[0120] Except using corresponding raw materials, compound 2 was prepared in the same manner as in Example 1, and the yield was 73.2%; 1 H-NMR (400MHz, CDCl 3 ):δ2.38(3H,s),3.69(6H,s),3.83(3H,s),6.28(1H,s),6.47(2H,s),7.01(2H,m),7.23(2H, m);MS(ESI):[M+H] + =343.1,[2M+Na] + =707.3.

Embodiment 3

[0121] Example 3: Preparation of 5-(4-methylphenyl)-3-methyl-1-(3,4,5-trimethoxyphenyl)-1H-pyrazole (compound 3)

[0122] Except using corresponding raw materials, compound 3 was prepared in the same manner as in Example 1, and the yield was 81.3%; 1 H-NMR (400MHz, CDCl 3 ):δ2.33(3H,s),2.38(3H,s),3.67(6H,s),3.83(3H,s),6.27(1H,s),6.50(2H,s),7.11(2H, d,J=8.28Hz),7.14(2H,d,J=8.28Hz);MS(ESI):[M+H] + =339.2,[2M+H] + =677.3,[2M+Na] + =699.3.

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Abstract

The invention belongs to the technical field of medicines and relates to a 3-methyl-1,5-diaryl pyrazole compound and an application thereof. In particularly, the invention relates to the applications of the compound in preparation of an anti-tumor drug as a tumor cell proliferation inhibitor. A structure of the 3-methyl-1,5-diaryl pyrazole compound is represented as follows, wherein R1-R9 are defined as in the specification. The compound and a composition containing the same have significant anti-tumor activities.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a 3-methyl-1,5-diarylpyrazole compound and its application. Specifically, it relates to the use of the compound as a tumor cell proliferation inhibitor in the preparation of anti-tumor drugs. aspects of application. Background technique [0002] Malignant tumors are serious diseases that threaten human health and life, and are one of the leading causes of death in China. Research and development of new anti-tumor drugs is a major issue at present. 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-trimethyl oxystyryl) phenol. CA-4 is an inhibitor of tubulin polymerization, which exhibits strong anti-tumor cell proliferation activity. Its prodrug CA-4 phosphate salt (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): C07D231/12C07D231/16A61P35/00
CPCC07D231/12C07D231/16
Inventor 张为革徐启乐吴英良文志勇关奇齐欢左代英张明亮翟延鹏
Owner SHENYANG PHARMA UNIVERSITY