5H-Dibenz[b,f]azepine based pyrazole sulphonamides: A privileged platform for probing the antimicrobial and antioxidative properties

Honnaiah Vijay Kumar; Prasanth Kumar; Javarappa Rangaswamy; Kirugunda Udayakumar Sindhu; Nagaraja Naik

doi:10.5155/eurjchem.6.4.394-403.1297

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Published: Dec 31, 2015

DOI: https://doi.org/10.5155/eurjchem.6.4.394-403.1297

Keywords:

Pyrazole, Sulphonamides, Antioxidant activity, Antimicrobial activity, 5H-Dibenz[b, f]azepine, Molecular docking studies

Section

Research Article

Issue

Vol. 6 No. 4 (2015): December 2015

Dates

Received 2015-07-02
Accepted 2015-08-09
Published 2015-12-31

Honnaiah Vijay Kumar

Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560012, Karnataka, India

Prasanth Kumar

Molecular and Biophysics Unit, Indian Institute of Science, Bangalore, 560012, Karnataka, India

Javarappa Rangaswamy

Department of Chemistry, Sarada Vilas College, Krishnamurthy Puram, Mysore, 570004, Karnataka, India

Kirugunda Udayakumar Sindhu

Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, Karnataka, India

Nagaraja Naik

Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, Karnataka, India

Abstract

In rummage around for a novel antimicrobial and antioxidant agent with improved potency, we designed and synthesized a series of 5H-dibenz[b,f]azepine based pyrazole sulphonamides (20-40) by expedient five steps route. All compounds were characterized by physico-chemical and spectroscopic techniques. In order to probe the antimicrobial and antioxidant activities, the newly synthesized compounds were assayed for their in vitro activities. Among the compounds of the particular interest, compounds 38 and 39 emerged as outperformed antimicrobial agents than standard streptomycin and fluconazole. Molecular docking studies of compound 38 and 39 into S. aureus tyrosyl-tRNA synthetase active site was performed, and the tight fitting of the compounds in the active site and the associated high binding energy might be the reason for their antimicrobial activity. On the other hand, compounds 28-30 were found to exert positive efficacy towards antioxidant activity comparable to butylated hydroxy anisole.

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Kumar, H. V.; Kumar, P.; Rangaswamy, J.; Sindhu, K. U.; Naik, N. 5H-Dibenz[b,f]azepine Based Pyrazole Sulphonamides: A Privileged Platform for Probing the Antimicrobial and Antioxidative Properties. Eur. J. Chem. 2015, 6, 394-403.

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NMR Research Center, Indian Institute of Science, Bangalore, India

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