Synthesis, crystal structure, Hirshfeld surface analysis and bioactivity studies of the hydrazones derived from 2-methylsulfonyl-5-nitrobezaldehyde against the breast (MCF-7) and cervical (HeLa) cancer cell lines, and their antioxidant potential.

Abstract

The hydrazones derived from 2-formyl-4-nitrophenyl methanesulfonate were characterized using a combination of spectroscopic and single crystal X-ray diffraction (XRD) techniques, in turn, evaluated for cytotoxicity in vitro against the human breast adenocarcinoma (MCF-7) and human cervical cancer (Hela) cell lines. The presence of a chlorine atom on the para position of the phenylhydrazone moiety of 3b resulted in increased cytotoxicity compared to camptothecin (IC₅₀ = 3.71 ± 0.16 µM and 9.15 ± 0.84 µM, respectively) against the Hela and MCF-7 cell lines with IC₅₀ values of 2.40 ± 0.13 µM and 5.64 ± 0.84 µM, respectively. The hydrazone derivatives exhibited significant 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity compared to ascorbic acid and 2-formyl-4-nitrophenyl methanesulfonate. Increased interactions of the arylhydrazone moiety are predicted with the residues in the active site of tyrosine kinase and cytochrome c peroxidase.