Regioselective synthesis and antitumor screening of some novel N-phenylpyrazole derivatives.
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.
Farag
Ahmad M
AM
Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt. afarag49@yahoo.com
Mayhoub
Abdelrahman S
AS
Barakat
Saber E
SE
Bayomi
Ashraf H
AH
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D020650:Combinatorial Chemistry Techniques; D004317:Doxorubicin / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D011720:Pyrazoles; C031280:pyrazole; D004317:Doxorubicin