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

• Main Authors: Mohamed J. Ahsan, Bhawani S. Kumawat, Sonu Kumawat, Piush Sharma, Mohammad A. Bakht, Mohd Z. Hassan, Afzal Hussain, Pankaj Saraswat, Habibullah Khalilullah
• Format: Article
• Language: English
• Published: Georg Thieme Verlag KG 2018-04-01
• Series: SynOpen
• Subjects: anticancer agents; breast cancer cell lines; mcf-7; mda-mb-231; srb assay; pyrazolines
• Online Access: http://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1591980

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.