Issue 1, 2023

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 N-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 via the conventional and microwave irradiation methods. Briefly, the new compounds 4(a–u) were synthesized via the N-alkylation of tetrahydro-1H-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 via 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.

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

Supplementary files

Article information

Article type
Paper
Submitted
21 Sep 2022
Accepted
24 Nov 2022
First published
19 Dec 2022
This article is Open Access
Creative Commons BY license

RSC Adv., 2023,13, 25-40

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

D. Ashok, G. Thara, B. K. Kumar, G. Srinivas, D. Ravinder, T. Vishnu, M. Sarasija and B. Sushmitha, RSC Adv., 2023, 13, 25 DOI: 10.1039/D2RA05960F

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