European Journal of Chemistry 2015, 6(4), 394-403 | doi: https://doi.org/10.5155/eurjchem.6.4.394-403.1297 | Get rights and content






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


Honnaiah Vijay Kumar (1,*) , Prasanth Kumar (2) , Javarappa Rangaswamy (3) , Kirugunda Udayakumar Sindhu (4) , Nagaraja Naik (5)

(1) Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560012, Karnataka, India
(2) Molecular and Biophysics Unit, Indian Institute of Science, Bangalore, 560012, Karnataka, India
(3) Department of Chemistry, Sarada Vilas College, Krishnamurthy Puram, Mysore, 570004, Karnataka, India
(4) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, Karnataka, India
(5) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, Karnataka, India
(*) Corresponding Author

Received: 02 Jul 2015 | Accepted: 09 Aug 2015 | Published: 31 Dec 2015 | Issue Date: December 2015

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.


Keywords


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

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DOI: 10.5155/eurjchem.6.4.394-403.1297

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Funding information


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

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How to cite


Kumar, H.; Kumar, P.; Rangaswamy, J.; Sindhu, K.; Naik, N. Eur. J. Chem. 2015, 6(4), 394-403. doi:10.5155/eurjchem.6.4.394-403.1297
Kumar, H.; Kumar, P.; Rangaswamy, J.; Sindhu, K.; 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(4), 394-403. doi:10.5155/eurjchem.6.4.394-403.1297
Kumar, H., Kumar, P., Rangaswamy, J., Sindhu, K., & Naik, N. (2015). 5H-Dibenz[b,f]azepine based pyrazole sulphonamides: A privileged platform for probing the antimicrobial and antioxidative properties. European Journal of Chemistry, 6(4), 394-403. doi:10.5155/eurjchem.6.4.394-403.1297
Kumar, Honnaiah, Prasanth Kumar, Javarappa Rangaswamy, Kirugunda Udayakumar Sindhu, & Nagaraja Naik. "5H-Dibenz[b,f]azepine based pyrazole sulphonamides: A privileged platform for probing the antimicrobial and antioxidative properties." European Journal of Chemistry [Online], 6.4 (2015): 394-403. Web. 6 Aug. 2020
Kumar, Honnaiah, Kumar, Prasanth, Rangaswamy, Javarappa, Sindhu, Kirugunda, AND Naik, Nagaraja. "5H-Dibenz[b,f]azepine based pyrazole sulphonamides: A privileged platform for probing the antimicrobial and antioxidative properties" European Journal of Chemistry [Online], Volume 6 Number 4 (31 December 2015)

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

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