New 1,2,4-Triazol Derivatives With 4-Fluorobenzene: Synthesis, Characterization, DFT, Antimicrobial-Antiproliferative Activities and Molecular Docking Study

Abstract

(E)-5-(4-fluorobenzyl)-4-((2-fluorobenzylidene)amino)-2,4-dihydro-3H-1,2,4-triazol-3-one (2F), (E)-5-(4-fluo- robenzyl)-4-((3-fluorobenzylidene)amino)-2,4-dihydro-3H-1,2,4-triazol-3-one (3F) and (E)-5-(4-fluorobenzyl)-4- ((4-fluorobenzylidene)amino)-2,4-dihydro-3H-1,2,4-triazol-3-one (4F) were synthesized and confirmed by FT-IR and 1H, 13CNMR spectroscopic methods. Theoretical study for compounds 2F -4F was performed by using DFT/ B3LYP/6-311++G(d,p) method. The optimized structures, IR and NMR data, the frontier molecular orbitals (HOMO and LUMO) and the molecular electrostatic potential (MEP) map of compounds 2F -4F were calculated. In addition, newly synthesized compounds (2F -4F) were tested against eight bacteria and two yeast strains and their the minimum inhibitory concentration (MIC) values were determined. The MTT test was performed to measure the antiproliferative effects of the 2F -4F compounds on cell proliferation (NCI-60 screening methodology). Molecular docking calculations were performed to investigate ligand-protein interactions between the compounds (2F and 3F) and the Epidermal Growth Factor Receptor (EGFR) and the Vascular Endothelial Growth Factor Receptor (VEGFR1).