Synthesis, characterization, computational chemical studies and antiproliferative activity of some heterocyclic systems derived from 3-(3-(1,3-diphenyl-1H-pyrazol-4-yl)acryloyl)-2H-chromen-2-one

Abstract

The key material, 3-(3-(1,3-diphenyl-1H-pyrazol-4-yl)acryloyl)-2H-chromen-2-one (3) was synthesized and its behavior toward malononitrile, hydrazine, thiourea, thiosemicarbazide, 2-aminoaniline, and 6-aminothiouracil was investigated aiming to synthesize a new series of pyrazole-based heterocycles, namely, pyranochromene, diazepine, pyrimidochromene, triazepine, benzodiazepine, pyrimidine, and pyrimidopyrimidine derivatives. Density functional theory based on quantum chemical computation outline the structure optimization of the intermediate that reacted to afford the desired product. The antiproliferative screening against HePG-2 and MCF-7 cancer cell lines disclosed that the most potent compounds against two cell lines were 9 and 17 as compared to doxorubicin which may be due to their presence in more tautomeric structures. Also, the minimized energy, dipole moment, ionization potential, transferred electrons, and charge density distribution revealed that the greater value of 0.126 and 0.8 for pyrazole derivatives 9 and 17, respectively, indicates the maximum transfer of electron and hence, greater tendency of scavenging radicals and rapidly reduce oxygen to superoxide.