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Original Article

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

Tutik Dwi Wahyuningsih, Artania Adnin Tri Suma, Endang Astuti.

Cited by 13 Articles

N-acetyl pyrazoline derivatives A-C containing methoxy and chloro/hydroxyl substituents were synthesized and tested for their anticancer 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 GC-MS, FTIR and NMR spectrometers. Cytotoxicity evaluation of pyrazolines revealed that pyrazoline A has moderate activity against breast cancer cell line MCF7 (IC50 40.47 µg/mL), T47D (IC50 26.51 µg/mL) and cervical cancer cell line HeLa (IC50 31.19 µg/mL). Pyrazoline B is inactive against all tested cancer lines (IC50 >100 µg/mL). Pyrazoline C has moderate activity against MCF7 (IC50 94.02 µg/mL), but inactive against T47D ad HeLa. Docking study showed the interaction between pyrazolines and EGFR receptor via hydrogen bonds and π-cation interactions.

Key words: anticancer, N-acetyl pyrazoline, chalcone, docking molecule, veratraldehyde, cyclocondensation

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