

5H-Dibenz[b,f]azepine based pyrazole sulphonamides: A privileged platform for probing the antimicrobial and antioxidative properties
Honnaiah Vijay Kumar (1,*)





(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.
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European Journal of Chemistry
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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
Citations
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Modelling the mechanism and kinetics of the radical scavenging activity of iminostilbene
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DOI: 10.1016/j.polymdegradstab.2021.109483

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[4]. Musa Erdoğan, Arif Daştan
Synthesis of N-substituted dibenzoazepine–pyridazine derivatives as potential neurologically active drugs
Synthetic Communications 50(24), 3845, 2020
DOI: 10.1080/00397911.2020.1828925

[5]. Maria Aqeel Khan, Farhana Batool, Asma Khatoon, Rabia Sadiq, Sher Rahman, Fatima Zehra Basha
Solvent-free protocol for the green synthesis of benzamide analogs of dibenzoazepine
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DOI: 10.5155/eurjchem.8.2.179-182.1567

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Cyclic voltammetry-assisted mechanistic evaluation of sulfonamide synthesis. A simple and green method for the synthesis of N-(1-hydroxynaphthalen-2-yl)benzenesulfonamide derivatives
Journal of Electroanalytical Chemistry 810, 161, 2018
DOI: 10.1016/j.jelechem.2018.01.001

[7]. Nguyen Thi Hoa, Nguyen Quang Trung, Nguyen Minh Thong, Adam Mechler, Quan V. Vo
The radical scavenging activity of monosubstituted iminostilbenes: Theoretical insights
Chemical Physics Letters 784, 139105, 2021
DOI: 10.1016/j.cplett.2021.139105

References
[1]. Lednicer, D. Strategies for Organic Drugs Synthesis and Design, 2nd edition, Wiley, Virgenia, 2008.
http://dx.doi.org/10.1002/9780470399613
[2]. Thansandote, P.; Lautens, M. Chem. A Eur. J. 2009, 15, 5874-5883.
http://dx.doi.org/10.1002/chem.200900281
[3]. Tsvelikhovsky, D.; Stephen L. B. J. Am. Chem. Soc. 2010, 132, 14048-14051.
http://dx.doi.org/10.1021/ja107511g
[4]. Singh, H.; Gupta, N.; Kumar, P.; Dubey, S. K.; Sharma, P. K. Org. Process Res. Dev. 2009, 13, 870-874.
http://dx.doi.org/10.1021/op900127v
[5]. Ambrosio, A. F.; Soares-Da-Silva, P. Neurochem. Res. 2002, 27, 121-130.
http://dx.doi.org/10.1023/A:1014814924965
[6]. Hirschfeld, R. M. A.; Kasper, S. Int. J. Neuropsychoph. 2004, 7, 507-522.
http://dx.doi.org/10.1017/S1461145704004651
[7]. Okuma, T.; Kishimoto, A. Psychiatry Clin. Neurosci. 1998, 52, 3-12.
http://dx.doi.org/10.1111/j.1440-1819.1998.tb00966.x
[8]. Gomez-Arguelles, J. M.; Dorado, R.; Sepulveda, J. M.; Huet, R.; Arrojo, F. G.; Aragon, E.; Herrera, A.; Trron, C.; Anciones, B. J. Clin. Neurosci. 2008, 15, 516-519.
http://dx.doi.org/10.1016/j.jocn.2007.04.010
[9]. Albani, F.; Riva, R.; Baruzzi, A. Pharmacopsychiat. 1995, 28, 235-244.
http://dx.doi.org/10.1055/s-2007-979609
[10]. Campbel, P. Nat. Insight. 2002, 415, 6872.
[11]. Anand, N. In Burger's Medicinal Chemistry and Drug Discovery. In Therapeutic Agents, 5th ed.; Wolff, M. E. J. Ed, Wiley Sons: New York, 1996.
[12]. Bouissane, L.; Kazzouli, E. S.; Leonce, S.; Pfeiffer, B.; Rakib, E. M.; Khouili, M. Bioorg. Med. Chem. 2006, 14, 1078-1088.
http://dx.doi.org/10.1016/j.bmc.2005.09.037
[13]. Melagraki, G.; Afantitis, A.; Sarimveis, H.; Igglessi- Markopoulou, O.; Supuran, C. T. Bioorg. Med. Chem. 2006, 14, 1108-1114.
http://dx.doi.org/10.1016/j.bmc.2005.09.038
[14]. Mandloi, D.; Joshi, S.; Khadikar, P. V.; Khosla, N. Bioorg. Med. Chem. Lett. 2005, 17, 405-411.
http://dx.doi.org/10.1016/j.bmcl.2004.10.076
[15]. Vullo, D.; Steffansen, B.; Brodin, B.; Supuran, C. T.; Scozzafava, A.; Nielsen, C. U. Bioorg. Med. Chem. 2006, 14, 2418-2427.
http://dx.doi.org/10.1016/j.bmc.2005.11.019
[16]. Sherif, A.; Rostom, F. Bioorg. Med. Chem. 2006, 14, 6475-6485.
http://dx.doi.org/10.1016/j.bmc.2006.06.020
[17]. Santos, M. A.; Marques, S. M.; Tuccinardi, T.; Carelli, P.; Panelli, L.; Rossello, A. Bioorg. Med. Chem. 2006, 14, 7539-7550.
http://dx.doi.org/10.1016/j.bmc.2006.07.011
[18]. Joshi, S.; Khosla, N.; Tiwari, P. Bioorg. Med. Chem. 2004, 12, 571-576.
http://dx.doi.org/10.1016/j.bmc.2003.11.001
[19]. Ortqvist, P.; Peterson, S. D.; Kerblom, A. E.; Gossas, T.; Sabnis, Y. A.; Fransson, R.; Lindeberg, G.; Danielson, U. H.; Karlen, A.; Sandstrom, A. Bioorg. Med. Chem. 2007, 15, 1448-1474.
http://dx.doi.org/10.1016/j.bmc.2006.11.003
[20]. Kumar, H. V.; Naik, N. Eur. J. Med. Chem. 2010, 45, 2-10.
http://dx.doi.org/10.1016/j.ejmech.2009.09.016
[21]. Kumar, H. V.; Kumar, C. K.; Naik, N. Med. Chem. Res. 2011, 20, 101-108.
http://dx.doi.org/10.1007/s00044-009-9292-7
[22]. Naik, N.; Sharath, V.; Kumar, H. V. Eur. J. Chem. 2012, 3, 214-219.
http://dx.doi.org/10.5155/eurjchem.3.2.214-219.588
[23]. Rangaswamy, J.; Kumar, H. V.; Harini, S. T.; Naik, N. Bioorg. Med. Chem. Lett. 2012, 22, 4773-4777.
http://dx.doi.org/10.1016/j.bmcl.2012.05.061
[24]. Naik, N.; Kumar, H. V.; Swamy, J. R. J. Pharm. Res. 2012, 5, 4504-4509.
[25]. Naik, N.; Kumar, H. V.; Harini, S. T. Eur. J. Chem. 2011, 2, 337‐341.
http://dx.doi.org/10.5155/eurjchem.2.3.337-341.363
[26]. Harini, S. T.; Kumar, H. V.; Rangaswamy, J.; Naik. N. Bioorg. Med. Chem. Lett. 2012, 22, 7588-7592.
http://dx.doi.org/10.1016/j.bmcl.2012.10.019
[27]. Arthington-Skaggs, B. A.; Motley, M.; Warnock, D. W.; Morrison, C. J. J. Clin. Microbiol. 2000, 38, 2254-2260.
[28]. Mac-Lowry, D. J.; Jaqua, M. J.; Selepak, S. T. Appl. Microbiol. 1970, 20, 46-53.
[29]. Vijesh, A. M.; Arun. M. I.; Peethambar, S. K.; Shivananda, K. N.; Arulmoli, T.; Nishitha, I. A. Eur. J. Med. Chem. 2011, 11, 5591-5597.
http://dx.doi.org/10.1016/j.ejmech.2011.09.026
[30]. Schuttelkopf, A. W.; VanAalten, D. M. F. Acta Cryst. D. 2004, 60, 1355-1363.
http://dx.doi.org/10.1107/S0907444904011679
[31]. Sobolev, V.; Sorokine, A.; Prilusky, J.; Abola, E. E. M. Bioinformatics 1999, 15, 327-332.
http://dx.doi.org/10.1093/bioinformatics/15.4.327
[32]. Blois, M. S. Nature. 1957, 181, 1199-1200
http://dx.doi.org/10.1038/1811199a0
[33]. Krichka, L. J.; Ledwith, A. Chem. Rev. 1974, 74, 101-123.
http://dx.doi.org/10.1021/cr60287a006
[34]. Yanagisawa, T.; Sumida, T.; Lshii, R.; Takemoto, C.; Yokoyama, S. Nat. Struct. Mol. Biol. 2010, 17, 1136-1143.
http://dx.doi.org/10.1038/nsmb.1889
[35]. Xu-Dong, W.; Rui-Cheng, D.; Jing-Jun, D.; Zhi-Yun, P.; Xiao-Ming, G.; Shu-Ting, L.; Wan-Qiang, L.; Chun-Lei, L.; Zhu-Ping, X.; Hai-Liang. Z. Bioorg. Med. Chem. 2013, 21, 4914-4922.
[36]. Morris, G. M.; Huey, R.; Lindstrom, W.; Sanner, M. F.; Belew, R. K.; Goodsell, D. S.; Olson, A. J. J. Comp. Chem. 2009, 16, 2785-2791.
http://dx.doi.org/10.1002/jcc.21256
[37]. Qiu, X.; Janson, C. A.; Smith, W. W.; Green, S. M.; McDevitt, P.; Johanson, K.; Carter, P.; Hibbs, M.; Lewis, C.; Chalker, A.; Fosberry, A.; Lalonde, J.; Berge, J.; Brown, P.; Houge-Frydrych, C. S.; Jarvest. R. L. Protein Sci. 2001, 10, 2008-2016.
http://dx.doi.org/10.1110/ps.18001
[38]. Jadhav, S. J.; Nimbalkar, S. S.; Kulkarani, A. D.; Madhavi, D. L. Food antioxidants, New York, CRC Press, 1996.
[39]. Mei, H. S.; Fang, Y. K. Bioorg. Med. Chem. 2004, 12, 4633-4643.
http://dx.doi.org/10.1016/j.bmc.2004.06.033
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