Synthesis, antioxidant activity, molecular docking, drug likeness and DFT studies of 1,2,4-triazole Schiff bases clubbed with heterocyclic moieties using Amberlite IR-4B as a catalyst

The need to develop powerful antioxidant agents capable of combating resistant infections without compromising human health has motivated significant research for novel antioxidant compounds. In this study, a series of simple 4-amino-5-methyl-4H-1,2,4-triazole-3-thiol-based Schiff bases were synthesized to investigate their potential as potent antioxidant agents. The methodology involved merging aromatic aldehydes, furan, pyrazole, chromone, and coumarin moieties into a single molecular framework, using Amberlite IR-4B as an acidic catalyst. The structures of compounds 2a–m were confirmed through various spectroscopic techniques and elemental analysis. Additionally, theoretical studies, including in silico computations using the Swiss ADME server, molecular modeling, and Density Functional Theory (DFT) calculations, provided further evidence of the efficiency and stability of the synthesized compounds. Among the series, compound 2b exhibited the most prominent antioxidant activity (2.25 ± 0.18 µg/mL), outperforming the standard. Moreover, molecular docking studies revealed that the investigated bioactive compounds occupy the same binding cavity as the well-known antioxidant ascorbic acid (ASC).