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

2007; Elsevier BV; Volume: 16; Issue: 2 Linguagem: Inglês

10.1016/j.bmc.2007.10.015

1464-3391

Ahmad M. Farag, Abdelrahman S. Mayhoub, Saber El‐Sayed Barakat, Ashraf H. Bayomi,

Bioactive Compounds and Antitumor Agents

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)acryloyl]-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.