Synthesis and characterization of some novel aryl and heteroaryl chalcone derivatives of 3-(3,4,5-trimethoxyphenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde for assessing their potentials as anticancer agents

Abstract

In the present study, a novel series of nine derivatives of 1-phenyl-3-(3,4,5-trimethoxyphenyl)-1H-pyrazole substituted chalcones 6a–6i were synthesized with an aim to assess their anticancer activities. The chalcone derivatives were synthesized by the Claisen condensation of 1-phenyl-3-(3,4,5-trimethoxyphenyl)-1H-pyrazole-4-carbaldehyde 4 with various aryl and heteroaryl acetophenones 5a–5i by treatment with alcoholic sodium hydroxide in methanol at reflux temperature in good to excellent yields. The newly synthesized derivatives were well characterized by IR, NMR, and HRMS spectroscopic techniques. The title compounds were evaluated for in vitro antibacterial activity against a panel of gram-positive and gram-negative bacteria and screened for anticancer activity employing EGFR lung protein based on in silico molecular docking studies. The study results showed IC₅₀ value ranging between 39–94 μg/mL compared to the standard Camptothecin with an IC₅₀ value of 47 μg/mL which indicates the anticancer potential of the majority of the synthesized compounds.