Regioselective synthesis and antitumor screening of some novel N-phenylpyrazole derivatives

被引:131
作者
Farag, Ahmad M. [1 ]
Mayhoub, Abdelrahman S. [2 ]
Barakat, Saber E. [2 ]
Bayomi, Ashraf H. [3 ]
机构
[1] Cairo Univ, Fac Sci, Dept Chem, Giza 12613, Egypt
[2] Al Azhar Univ, Fac Pharm, Dept Pharmaceut Chem, Giza 11884, Egypt
[3] Al Azhar Univ, Fac Pharm, Dept Organ Chem, Giza 11884, Egypt
关键词
phenylcarbamoyl-1H-pyrazole; 1,3-dipolar cycloaddition; nitrilimines; cytotoxicity; antitumor agent; N-phenylpyrazoles; regioselective synthesis; antitumor activity; dimethylformamide-dimethylacetal (DMF-DMA); enaminones; structure-activity relationship (SAR);
D O I
10.1016/j.bmc.2007.10.015
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The versatile, hitherto unreported 4-acetyl-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole (3) was prepared via the reaction of 2-(2-phenylhydrazono)-2-chloro-N-phenylacetamide with pentan-2,4-dione in the presence of sodium ethoxide. Reaction of 3 with dimethylformamide-dimethylacetal (DMF-DMA) furnished the corresponding 4-[(E)-3-(dimethylamino)aci-yloyl]-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole (5). The latter product underwent regioselective 1,3-dipolar cycloaddition with some nitrilimines to afford the non-isolable dihydropyrazole intermediates which then lose dimethylamine yielding the corresponding pyrazole derivatives. The preliminary screening for the antitumor activity of all newly synthesized compounds was carried out against Ehrlich Ascites Carcinoma tumor cells. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:881 / 889
页数:9
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