Microwave-assisted synthesis, molecular docking studies of 1,2,3-triazole-based carbazole derivatives as antimicrobial, antioxidant and anticancer agents

Abstract

Herein, a new series of <i>N</i>-substituted 1,2,3-triazolylmethyl indole derivatives 4(a-u) was synthesized by rationally incorporating a pharmacophoric active heterocyclic ring containing indole and triazole moieties in one molecular frame <i>via</i> the conventional and microwave irradiation methods. Briefly, the new compounds 4(a-u) were synthesized <i>via</i> the <i>N</i>-alkylation of tetrahydro-1<i>H</i>-carbazoles followed by click reaction and copper-catalyzed Huisgen [3 + 2] cycloaddition in the presence of copper sulphate and sodium ascorbate with various aromatic azides 3(a-m). All the newly synthesized compounds were characterized <i>via</i> ¹H and ¹³C NMR, mass, and IR spectroscopy and evaluated for their antimicrobial, antioxidant and anticancer activities. Among the synthesized compounds, 4d, 4j, 4n, 4p, 4s and 4r were found to exhibit good antimicrobial, antioxidant, anticancer activities. The biological activity of the synthesized compounds was further supplemented by molecular docking studies against the target receptors caspase-3 and 17-beta-hydroxy steroid dehydrogenase type 1, revealing that the reported structures best fit into the active site pocket of the target molecules.