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 andtested for their cytotoxic activities. The precursor chalcones A–C which were obtained from the condensation reactionbetween veratraldehyde and acetophenone derivatives were reacted with hydrazine hydrate in the presence of glacialacetic acid to give pyrazolines A–C with excellent yield and purity. Characterization of all products was done usingFourier 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 breastcancer cell line MCF7 (IC50 40.47 µg/ml), breast cancer cell line T47D (IC50 26.51 µg/ml), and cervical cancer cell lineHeLa (IC50 31.19 µg/ml). Pyrazoline B is inactive against all tested cancer lines (IC50 > 100 µg/ml). Pyrazoline C hasmoderate activity against MCF7 (IC50 94.02 µg/ml), but inactive against T47D and HeLa. Docking study showed theinteraction between pyrazolines and EGFR receptor via hydrogen bonds and π-cation interactions.