New phenylisoxazole derivatives: Synthesis, spectroscopic, X-ray, IR, DFT calculation and biological activity studies

Abstract

A series of new phenylisoxazole derivatives were successfully designed and synthesized for developing antitumor compounds. The final compounds were characterized through 1HNMR , 13CNMR , and HRMS. Moreover, (Z)-2-(5-((3-(4-bromophenyl)isoxazole-4-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)-N-cyclopentylacetamide (5a) was confirmed by FT-IR and X-ray single crystal diffraction (XRD). The density functional theory (DFT) calculation of compound 5a was carried out at the B3LYP/6–311 level. The calculated parameters were in good agreement with the real experimental structures. The frontier molecular orbitals (FMO) and the molecular electrostatic potential (MEP) of compound 5a were also calculated and discussed. In addition, the antitumor activity of the ten compounds was evaluated by MTT assay against A549 cell.