Synthesis, Characterization, Molecular Docking, and DFT Studies of 2,3,5-Trisubstituted-1,3,4-Oxadiazol-3(2H)-yl Methanone Derivatives

2, 3, 5-Trisubstituted-1, 3, 4-Oxadiazol-3-(2H)-yl methanone derivatives are synthesized and characterized by spectral methods such as IR, 1 H NMR, [Formula: see text]C NMR and MS. The molecular docking study was conducted with assorted bacterial and fungal target proteins (PDB Id: 2ZCO, 1SNN, 1CVU, 3OSV, 6IV7 and 7BLY) to study the binding interactions of synthesized compounds. Scaffold 2[Formula: see text] exhibited the best docking scores of –10.5, –10.0, –9.5 and –10.5 kcal/mol against target proteins 1CVU, 2ZCO, 3OSV and 7BLY, respectively. Further, synthesized analogs showed good to moderate anti-bacterial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa; and anti-fungal activity againstAspergillus nigerandCandida albicans. Remarkably, 2[Formula: see text] and 2[Formula: see text] showed auspicious anti-fungal and anti-bacterial activity compared to other molecules. The DFT study was carried out at the level of B3LYP/6-31G (s) to obtain the optimized geometry of molecules, frontier molecular orbital energies, molecular electrostatic potential plots and global reactivity parameters ([Formula: see text] and [Formula: see text] to explore their structural and electronic features. Compound 2[Formula: see text] exhibited the highest reactivity ([Formula: see text]: 1.454 eV) and compound 2[Formula: see text] exhibited the lowest toxicity ([Formula: see text]: 1.401 eV) among all analogs. Overall, these findings indicate that compounds 2[Formula: see text], 2[Formula: see text] and 2[Formula: see text] would be prominent intrants for further studies concerning research and development as they exhibit good anti-microbial activity, best docking scores and favorable [Formula: see text], [Formula: see text] and [Formula: see text] parameters.