New N-phenylacetamide-incorporated 1,2,3-triazoles: [Et3NH][OAc]-mediated efficient synthesis and biological evaluation

Satish V. Akolkar; Amol A. Nagargoje; Vagolu S. Krishna; Dharmarajan Sriram; Jaiprakash N. Sangshetti; Manoj Damale; Bapurao B. Shingate

doi:10.1039/C9RA03425K

New N-phenylacetamide-incorporated 1,2,3-triazoles: [Et₃NH][OAc]-mediated efficient synthesis and biological evaluation†

Satish V. Akolkar,

^a Amol A. Nagargoje,^a Vagolu S. Krishna,^b Dharmarajan Sriram,^b Jaiprakash N. Sangshetti,

^c Manoj Damale^d and Bapurao B. Shingate*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad 431 004, India
E-mail: bapushingate@gmail.com
Fax: +91-240-2403113
Tel: +91-240-2403313

^b Department of Pharmacy, Birla Institute of Technology & Science-Hyderabad Campus, Jawahar Nagar, Hyderabad 500 078, India

^c Department of Pharmaceutical Chemistry, Y. B. Chavan College of Pharmacy, Dr. Rafiq Zakaria Campus, Aurangabad 431 001, India

^d Department of Pharmaceutical Chemistry, Srinath College of Pharmacy, Aurangabad 431136, MS, India

Abstract

A facile, highly efficient, and greener method for the synthesis of new 1,4-disubstituted-1,2,3-triazoles was conducted using [Et₃NH][OAc] as a medium by the implementation of ultrasound irradiation via click chemistry, affording excellent yields. The present synthetic method exhibited numerous advantages such as mild reaction conditions, excellent product yields, minimal chemical waste, operational simplicity, shorter reaction time, and a wide range of substrate scope. The synthesized compounds were further evaluated for in vitro antifungal activity against five fungal strains, and some of the compounds displayed equivalent or greater potency than the standard drug. A molecular docking study against the modelled three-dimensional structure of cytochrome P450 lanosterol 14α-demethylase was also performed to understand the binding affinity and binding interactions of the enzyme. Furthermore, the synthesized compounds were evaluated for DPPH radical scavenging activity and antitubercular activity against Mycobacterium tuberculosis H37Rv strain.

This article is part of the themed collection: A Decade of Progress in Click Reactions Based on CuAAC

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Article information

DOI: https://doi.org/10.1039/C9RA03425K
Article type: Paper
Submitted: 07 May 2019
Accepted: 27 Jun 2019
First published: 18 Jul 2019
This article is Open Access

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RSC Adv., 2019,9, 22080-22091

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New N-phenylacetamide-incorporated 1,2,3-triazoles: [Et₃NH][OAc]-mediated efficient synthesis and biological evaluation

S. V. Akolkar, A. A. Nagargoje, V. S. Krishna, D. Sriram, J. N. Sangshetti, M. Damale and B. B. Shingate, RSC Adv., 2019, 9, 22080 DOI: 10.1039/C9RA03425K

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