Synthesis of N-Asetilpirazolina-Based Veratraladehida and 2-Hidroksiasetofenon and selectivity Against Some Cancer Cells
ABSTRACT: Synthesis and cytotoxicity test of N-acetylpyrazoline have been carried out. First, chalcone was synthesized from veratraldehyde and 2-hydroxyacetophenone in methanol using NaOH 40% (w/v) under reflux for 4 hours. Second, synthesis of N-acetylpyrazoline was conducted by refluxing the chalcone and hydrazine monohydrate in the presence of excessive glacial acetic acid for 24 hours. The structure elucidation of products was confirmed by FTIR, GC-MS, 1H-, 13C- and HMQC-NMR spectrometers. Cytotoxicity tests of chalcone and N-acetylpyrazoline against MCF-7, HeLa, T47D and WiDr cancer cells also Vero cell line were conducted by MTT assay. The product of chalcone [(E)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl) prop-2-en-1-one] had m.p of 103.2-106.0 oC in 45.07% yield, while N-acetylpyrazoline [1-(5-(3,4-dimethoxyphenyl)-3-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone] was yielded in 93.14% as white solid with m.p of 137.4-139.8 ����¯�¿�½���¯���¿���½������¯������¿������½����¯�¿�½������¯����¯�¿�½������¿����¯�¿�½������½����¯�¿�½���¯���¿���½����¯�¿�½������¯����¯�¿�½���¯���¿���½����¯�¿�½������¿����¯�¿�½���¯���¿���½����¯�¿�½������½����¯�¿�½���¯���¿���½������¯������¿������½����¯�¿�½������¯����¯�¿�½������¿����¯�¿�½������½����¯�¿�½���¯���¿���½������¯������¿������½����¯�¿�½���¯���¿���½����¯�¿�½������ºC. The N-acetylpyrazoline had moderate toxicity against MCF-7 cells, weak toxicity against HeLa and WiDr cells and no toxicity towards T47D cells. Therefore, the N-acetylpyrazoline activity against MCF-7 cancer cells was more selective than WiDr, HeLa and T47D cells. The chalcone also showed better selectivity to MCF-7 cells and more toxic than N-acetylpyrazoline. The low toxicities of N-acetylpyrazoline was probably due to the presence of hydroxyl group at orto position. Keywords: N-acetylpyrazoline, chalcone, cytotoxicity, veratraldehyde
