Synthesis, anticancer activity, and docking study of N-acetyl pyrazolines from veratraldehyde

Abstract

N-acetyl pyrazoline derivatives A-C containing methoxy and chloro/hydroxyl substituents were synthesized and tested for their cytotoxic activities. The precursor chalcones A-C which were obtained from the condensation reaction between veratraldehyde and acetophenone derivatives were reacted with hydrazine hydrate in the presence of glacial acetic acid to give pyrazolines A-C with excellent yield and purity. Characterization of all products was done using Fourier transform infrared (FTIR), nuclear magnetic resonance (NMR) and gas chromatography-mass spectrometers. (GC-MS). Cytotoxicity evaluation of pyrazolines revealed that pyrazoline A has moderate activity against breast cancer cell line MCF7 (IC 50 40.47 g/ml), breast cancer cell line T47D (IC 50 26.51 g/ml), and cervical cancer cell line HeLa (IC 50 31.19 g/ml). Pyrazoline B is inactive against all tested cancer lines (IC 50 > 100 g/ml). Pyrazoline C has moderate activity against MCF7 (IC 50 94.02 g/ml), but inactive against T47D and HeLa. Docking study showed the interaction between pyrazolines and EGFR receptor via hydrogen bonds and -cation interactions.