European Journal of Chemistry

ZnBr2-SiO2 catalyzed green synthesis of tetrazoles: Molecular docking and antioxidant activity studies



Main Article Content

Chenna Krishna Reddy Reddivari
Subba Rao Devineni
Jyothi Kumar Malaka Venkateshwarulu
Vijaya Bhaskar Baki
Appa Rao Chippada
Rajendra Wudayagiri
Rami Reddy Yallala Venkata
Naga Raju Chamarthi

Abstract

A series of 5-substituted and 1,5-disubstituted tetrazoles were synthesized in high yields from various biologically active substituted nitriles with sodium azide under heterogeneous catalysed (ZnBr2-SiO2) [2+3] cycloaddition conditions. This reaction gave an excellent yield in the presence of catalytic amount of 0.2 g of ZnBr2-SiO2, glycerol solvent system under microwave irradiation conditions. All the prepared compounds were characterized by elemental analysis 1H NMR, 13C NMR, FT-IR, and mass spectral data. The newly synthesized compounds were investigated for their respective molecular target using molecular docking studies. The results reveal that compounds 5a, 5c, 5e and 3e have conferred with multi target property. The compounds 5a, 5c and 5e have shown the highest binding affinities of -10.1, -9.7 and -10.6 with reverse transcriptase, -8.5, -8.2 and -8.9 with Aurora B, respectively. The compounds 5a, 5e and 3e have shown -8.9, -8.5 and 8.4 with Aromatase, respectively. In addition, the antioxidant activity data reveals that all the compounds showed good antioxidant activity, particularly the compounds 3d, 5d, and 5e exhibited promising radical scavenging activity.


icon graph This Abstract was viewed 2325 times | icon graph Article PDF downloaded 770 times

How to Cite
(1)
Reddivari, C. K. R.; Devineni, S. R.; Venkateshwarulu, J. K. M.; Baki, V. B.; Chippada, A. R.; Wudayagiri, R.; Venkata, R. R. Y.; Chamarthi, N. R. ZnBr2-SiO2 Catalyzed Green Synthesis of Tetrazoles: Molecular Docking and Antioxidant Activity Studies. Eur. J. Chem. 2017, 8, 66-75.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Katritzky, A. R.; Rees, C. W. In Comprehensive Heterocyclic Chemistry II, Pergamon Press, Oxford, 1984.

[2]. Butler, R. N.; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V. In Comprehensive Heterocyclic Chemistry II, Pergamon Press, Oxford, 1996.

[3]. Noda, K.; Saad, Y.; Kinoshita, A.; Boyle, T. P.; Graham, R. M.; Husain, A.; Karnik, S. S. J. Biol. Chem. 1995, 270, 2284-2289.
https://doi.org/10.1074/jbc.270.5.2284

[4]. Monn, J. A.; Valli, M. V.; True, R. A.; Schoepp, D. D.; Leander, J. D.; Lodge, D. Bioorg. Med. Chem. Lett. 1993, 3, 95-98.
https://doi.org/10.1016/S0960-894X(00)80099-2

[5]. Daya, S.; Kaye, P. T.; Mphahlele, M. J. Med. Sci. Res. 1996, 24, 137-141.

[6]. Huang, R. Q.; Bell-Horner, C. L.; Dibas, M. I.; Covey, D. F.; Drewe, J. A.; Dillon, G. H. J. Pharmacol. Exp. Ther. 2001, 298, 986-995.

[7]. Chester, J. A.; Coon, L. E. Pharmacol. Biochem. Behav. 2010, 95, 258-265.
https://doi.org/10.1016/j.pbb.2010.02.001

[8]. Davis, B.; Brandstetter, T. W.; Smith, C.; Hackett, L.; Winchester, B. G.; Fleet, G. W. J. Tetrahedron Lett. 1995, 36, 7507-7510.
https://doi.org/10.1016/0040-4039(95)01518-3

[9]. Wu, S.; Fluxe, A.; Sheffer, J.; Janusz, J. M.; Blass, B. E.; White, R.; Jackson, C.; Hedges, R.; Muawsky, M.; Fang, B.; Fadayel, G. M.; Hare, M.; Djandjighian, L. Bioorg. Med. Chem. Lett. 2006, 16, 6213-6218.
https://doi.org/10.1016/j.bmcl.2006.09.021

[10]. Momose, Y.; Maekawa, T.; Odaka, H.; Ikeda, H.; Sohda, T. Chem. Pharm. Bull. 2002, 50, 100-111.
https://doi.org/10.1248/cpb.50.100

[11]. Upadhayaya, R. S.; Jain, S.; Sinha, N.; Kishore, N.; Chandra, R.; Arora, S. K. Eur. J. Med. Chem. 2004, 39, 579-592.
https://doi.org/10.1016/j.ejmech.2004.03.004

[12]. Ikeda, T.; Kakegawa, H.; Miyataka, H.; Matsumoto, H.; Satoh, T. Bioorg. Med. Chem. Lett. 1992, 7, 709-714.
https://doi.org/10.1016/S0960-894X(00)80397-2

[13]. Brauner-Osborne, H.; Egebjerg, J.; Nielsen, E. O.; Madsen, U.; Krogsgaard-Larsen, P. J. Med. Chem. 2000, 43, 2609-2645.
https://doi.org/10.1021/jm000007r

[14]. Lusina, M.; Cindric, T.; Tamaic, J.; Peko, M.; Pozaic, L.; Musulin, N. Int. J. Pharm. 2005, 291, 127-137.
https://doi.org/10.1016/j.ijpharm.2004.07.050

[15]. Duncia, J. V.; Pierce, M. E.; Santellalll, J. B. J. Org. Chem. 1991, 56, 2395-2400.
https://doi.org/10.1021/jo00007a027

[16]. Sandmann, G.; Schneider, C.; Boger, P. Z. Naturforsch. C. 1996, 51, 534-538.

[17]. Koldobskii, G. I.; Ostrovskii, V. A.; Poplavskii, V. S. Khim. Geterotsikl. Soedin. 1981, 10, 1299-1326.

[18]. Ostrovskii, V. A.; Koldobskii, G. I. Ros. Khim. Zh. 1997, 41, 84.

[19]. Chermahini, Z. J.; Chermahini, A. N.; Dabbagh, H. A.; Teimouri, A. J. Ener. Chem. 2015, 24, 770-778.
https://doi.org/10.1016/j.jechem.2015.10.015

[20]. Zhao, Y. P.; Li, Y.; Wang, S. H.; Xu, J. G.; Yan, Y.; Zheng, F. K.; Guo, G. C. Inorg. Chem. Comm. 2016, 68, 56-59.
https://doi.org/10.1016/j.inoche.2016.04.008

[21]. Moore, D. S.; Robinson, S. D. Adv. Inorg. Chem. 1988, 32, 171-239.
https://doi.org/10.1016/S0898-8838(08)60232-9

[22]. Gutmann, B.; Roduit, J. P.; Roberge, D.; Kappe, C. O. Angew. Chem. Int. Ed. 2010, 49, 7101-7105.
https://doi.org/10.1002/anie.201003733

[23]. Amantini, D.; Beleggia, R.; Fringuelli, F.; Pizzo, F.; Vaccoro, L. J. Org. Chem. 2004, 69, 2896-2898.
https://doi.org/10.1021/jo0499468

[24]. Grzonka, Z.; Liberek, B. Roczniki. Chemii. 1971, 45, 967-980.

[25]. Kant, R.; Singh, V.; Agarwal, A. Comptes. Rendus. Chimie. 2016, 19, 306-313.
https://doi.org/10.1016/j.crci.2015.11.016

[26]. Demko, Z. P.; Sharpless, K. B.; J. Org. Chem. 2001, 66, 7945-7950.
https://doi.org/10.1021/jo010635w

[27]. Patil, V. S.; Nandre, K. P.; Borse, A. U.; Bhosale, S. V. E-J. Chem. 2012, 9, 1145-1152.

[28]. Caddick, S. Tetrahedron1995, 51, 10403-10432.
https://doi.org/10.1016/0040-4020(95)00662-R

[29]. Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis1998, 9, 1213-1234.
https://doi.org/10.1055/s-1998-6083

[30]. Trott, O.; Olson, A. J. J. Comput. Chem. 2010, 31, 455-461.

[31]. Wolf, L. K. PyRx C&EN 2009, 87, 31-48.

[32]. DeLano, W. L. The PyMOL Molecular Graphics System. DeLano Scientific, San Carlos, CA, USA.

[33]. Bhaskar, V. B.; Babu, T. M. C.; Reddy, N. V.; Rajendra, W. Drug Des. Devel. Ther. 2016, 10, 3237-3252.
https://doi.org/10.2147/DDDT.S113556

[34]. Sekhar, K. C.; Syed, R.; Golla, M.; Kumar, M. V. J.; Yellapu, N. K.; Chippada, A. R.; Chamarthi, N. R. DARU. J. Pharm. Sci. 2014, 22, 76-90.

[35]. Mallesha, L.; Mohana, K. N. Eur. J. Chem. 2011, 2, 193-199.
https://doi.org/10.5155/eurjchem.2.2.193-199.282

[36]. Marcocci, L.; Maguire, J. J.; Droy-Lefaix, M. T.; Packer, L. Biochem. Biophys. Res. Commun. 1994, 201, 748-55.
https://doi.org/10.1006/bbrc.1994.1764

[37]. Nabavi, S. M.; Ebrahimzadeh, M. A.; Nabavi, S. F.; Hamidinia, A.; Bekhradnia, A. R. Pharmacologyonline 2008, 2, 560-567.

Supporting Agencies

University Grants Commission (UGC) and Department of Chemistry, Sri Venkateswara University, Tirupati, 517502, India
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).