Novel 1,2,3-triazole compounds: Synthesis, In vitro xanthine oxidase inhibitory activity, and molecular docking studies

Abstract

In this study, novel 1,2,3-triazole compounds containing carbasugar frameworks (5 and 6) were synthesized by the copper-catalyzed azide-alkyne cycloaddition reactions and their in vitro inhibition effects on the enzyme xanthine oxidase were investigated. All of the synthesized compounds were characterized by spectroscopic methods. According to the enzyme inhibition results, compounds 5 (IC50 = 0.586 +/- 0.017 mu M) and 6 (IC50 = 0.751 +/- 0.021 mu M) showed stronger inhibition effects than allopurinol (IC50 = 1.143 +/- 0.019 mu M), which is a standard drug used for inhibition of xanthine oxidase. The binding modes of the 1,2,3-triazole compounds (5 and 6) with the active site of xanthine oxidase were explained based on molecular docking studies. The molecular docking studies showed that the aromatic structure, pi-pi interactions and hydrophobic interactions play a major role in xanthine oxidase inhibition for compounds 5 and 6. (C) 2020 Elsevier B.V. All rights reserved.