Synthesis and Cytotoxic Evaluation of 3-(4-Fluorophenyl)-4,5-dihydro-5-(3,4,5-trimethoxy/4-nitrophenyl)-N-(substituted-phenyl)pyrazole-1-carboxamide Analogues

Abstract

A novel series of 3-(4-fluorophenyl)-4,5-dihydro-5-(3,4,5-trimethoxy/4-nitro phenyl)-N-(substituted-phenyl)pyrazole-1-carboxamide analogues 4a–n was synthesized in two steps from 4-fluoroacetophenone. The pyrazoline analogues were evaluated for cytotoxicity against two breast cancer cell lines (MCF-7 and MBA-MD-231) by the sulforhodamine B (SRB) assay. N-(4-Chlorophenyl)-3-(4-fluorophenyl)-5-(4-nitrophenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide (4b) showed the most promising cytotoxicity among the series, with GI₅₀ <0.1 and 45.8 μM against the cancer cell lines, MCF-7 and MDA-MB-231, respectively. The anticancer activity of 4b was found to be comparable to that of the standard drug adriamycin (GI₅₀ <0.1) against the MCF-7 cancer cell line. Structure activity relationships (SAR) are also considered.

Key words

anticancer agents - breast cancer cell lines - MCF-7 - MDA-MB-231 - SRB assay - pyrazolines

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