Synthesis, Characterization, Antimicrobial Activity, and Docking Study of Some 1,3,4-Oxadiazole Derivatives with Tert-Amine Moiety

The alkylation of 5-(((4-bromophenyl) (3,4,5-trimethoxybenzyl) amino) methyl)-1,3,4-oxadiazole-2(3H)-thione was successfully achieved through an alkylation reaction in absolute ethanol. Six alkyl halides were utilized in K2CO3 (anhydrous) medium at room temperature. 1H NMR, 13C NMR, FTIR and EIMs are used to characterize the resulting compounds. Antibacterial activity assay was conducted on all compounds against S. aureus and E. coli bacteria which displayed significant antibacterial activities. Molecular docking was employed to prioritize compounds for assessing their potential to bind to the target of interest. Each compound exhibited a significant decrease in binding free energy (ΔG) compared to the co-crystallized ligand (human PPARα agonist). The heterocyclic compounds demonstrated an effect on peroxisome proliferator-activated alpha receptors, which are utilized in the treatment of hyperlipidemia. Consequently, the synthetic compounds containing a thioalkyl group, a para-bromobenzene group, as well as a 3,4,5-trimethoxybenzyl group, exhibited an enhanced activity on PPARα receptors.