Synthesis and Biological Evaluation of Substituted Pyrazoline Derivatives Bearing 3,4,5-Trimethoxyphenyl Moiety as Anticancer, Anti-inflammatory and Antioxidant Agents

In search for a potent agent, 3-(4-nitrophenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole 3a with the chalcone scaffold (E)-1-(4-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 2a was synthesized to design 3-(4-nitrophenyl)-1-substituted phenyl-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole 4a-e and 3-(4-nitrophenyl)-N-substituted phenyl-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide 5a-e. IR, 1H NMR and mass spectral analysis, confirmed the structure of compounds. All compounds evaluated for in vitro anticancer, anti-inflammatory and antioxidant activity. Among the series, compound 3a and 5b found to possess potent anticancer activity against breast carcinoma (MCF7). The data for antioxidant activity revealed that, compound 4b and 5c exhibited significant 1,1-Diphenyl-2-picryl-hydrazyl (DPPH) radical scavenging activity as compared to the standard drug ascorbic acid. Compounds 2a, 4d and 5b showed excellent nitric oxide radical scavenging activity. While, compounds 2a, 4e, 5a, 5b and 5c showed pronounced superoxide radical scavenging activity, However all the compounds tested for H2O2 radical scavenging activity were devoid of activity. Additionally, compounds 4b, 4d, 4e and 5b showed good anti-inflammatory activity.