Synthesis, density functional theory, and cytotoxic activity of some heterocyclic systems derived from 3-(3-(1,3-diphenyl-1H-pyrazol-4-yl)acryloyl)-2H-chromen-2-one

Abstract

The behavior and reactivity of a coumarin-based chalcone bearing a pyrazole core 3 toward malononitrile, hydrazine, thiourea, hydrazinecarbothioamide, 2-aminoaniline, and 6-aminothiouracil were investigated as an attempt to design and synthesize a novel series of pyrazole-based heterocycles, viz. pyranocoumarin, diazepine, pyrimidochromene, triazepine, benzodiazepine, and pyrimidopyrimidine derivatives. DFT based on quantum chemical computation outlines the structure optimization of the intermediate that reacted to achieve the desired product. The antitumor activity 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 attributed to their presence in more tautomeric structures. Also, the minimized energy, dipole moment, ionization potential, transferred electrons, and charge density distribution disclosed 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.