Nonsteroidal Anti-inflammatory Drug-based N-Allylidene Benzohydrazides and 1-Acyl-2-pyrazolines: Their Synthesis as Potential Cytotoxic Agents In Vitro

A series of 1-acyl-2-pyrazoline derivatives derived from nonsteroidal anti-inflammatory drugs was designed as potential anticancer agents. Synthesis of these compounds was carried out via the condensation reaction of chalcones and acid hydrazides under heating. The methodology did not require the use of any costly reagents or catalysts, and the acid hydrazide reactants were readily prepared from mefenamic acid or ibuprofen. A variety of 1-acyl-2-pyrazolines was prepared in good to excellent yields. An N-allylidene benzohydrazide intermediate was isolated during the reaction optimization study, the structure of which was confirmed unambiguously by X-ray single crystal data. A range of N-allylidene benzohydrazides were also prepared in good yields. Some of the compounds synthesized showed promising cytotoxic activities when tested against HCT-15 human colon cancer cell line in vitro.