Dibenzyl amine as an ammonia surrogate in the Ugi tetrazoles: Design, synthesis and impactful antioxidant activity

Abstract

In this study, we develop novel tetrazole compounds based on dibenzyl amine (DBA) and investigate their potential as antioxidants. The aforementioned compounds were synthesised by the Ugi multicomponent reaction, which involved the simultaneous addition of four systems, i.e., DBA, cyclohexyl isocyanide, TMSN3 and aromatic aldehyde in ethanol media under RT. The different isocyanides effect in the progress of the TMSN3 based Ugi reaction was studied. The tetrazoles that were changed with DBA were studied using several techniques, including FTIR, 1H NMR, 13C NMR, and MS. The antioxidant properties of the produced compounds (4a-4j) were subsequently tested in a controlled laboratory setting using the 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) free radical assay. When compared to ascorbic acid, the antioxidant efficacy of all of the produced compounds was high. The obtained results for all prepared compounds were good as an antioxidant in comparison with ascorbic acid. The electron withdrawing effect of the substituents (halogens and nitro groups) on the aromatic side enhanced the antioxidant activity of the newly derived motifs. Their molecular docking investigation with the myeloperoxidase (MPO) enzyme revealed a strong relationship between their binding modalities and the antioxidant properties they displayed.