Cytotoxic potential of novel N-formyl pyrazolines derived from vanillin

In the reaction of vanillin and acetone under Claisen-Schmidt conditions, dehydrozingerone, a very attractive biologically active compound, is obtained. This compound served as a starting material for the synthesis of O-alkyl derivatives which further react with hydrazine hydrate in formic acid, yielding a new series of N-formyl pyrazolines. All new products were identified and well characterized by IR, 1H NMR, and 13C NMR spectroscopy. An ADME study was performed to investigate the pharmacokinetic properties of the synthesized derivatives. The preliminary in vitro cytotoxic activity of pyrazolines against the human cervix adenocarcinoma cell line (HeLa) was evaluated using the MTT method. Among the series, compounds 3c, 3d and 3f showed the most promising cytotoxic activity. Morphology changes of HeLa cells treated with selected compounds were visualized and compared with that of the control.