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Click Synthesis of Some mono/bis 1,2,3-Triazoles with Ester Linkage and their Microbicidal Activity
Corresponding Author(s) : C.P. Kaushik
Asian Journal of Chemistry,
Vol. 29 No. 10 (2017): Vol 29 Issue 10
Abstract
Synthesis of some new 1,4-disubstituted 1,2,3-triazoles with ester functionality is reported employing Cu(I) catalyzed Huisgen [3+2] cycloaddition reaction of prop-2-yn-1-yl benzoates with 1,4-phenylenebis(methylene) bis(2-azidoacetate) and benzyl 2-azidoacetates. The synthesized compounds were well characterized through FTIR, 1H NMR, 13C NMR and HRMS. Further, the synthesized triazole derivatives were accessed for in vitro antimicrobial activity against one Gram-positive bacterial strain Staphylococcus aureus, three Gram-negative bacterial strains Escherichia coli, Klebsiella pneumoniae, Enterobacter aerogenes and two fungi Candida albicans and Aspergillus niger. Few of the synthesized disubstituted 1,2,3-triazoles displayed moderate to good inhibitory activity against tested microbial strains.
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- M.K. Singh, M. Gangwar, D. Kumar, R. Tilak, G. Nath and A. Agarwal, Med. Chem. Res., 23, 4962 (2014); https://doi.org/10.1007/s00044-014-1063-4.
- C.P. Kaushik, A. Pahwa, R. Thakur and P. Kaur, Synth. Commun., 47, 368 (2017); https://doi.org/10.1080/00397911.2016.1265983.
- A. Ouahrouch, M. Taourirte, D. Schols, R. Snoeck, G. Andrei, J.W. Engels and H.B. Lazrek, Arch. Pharm. Chem. Life Sci., 348, 1 (2015); https://doi.org/10.1002/ardp.201500292.
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- C.P. Kaushik, K. Kumar, D. Singh, S.K. Singh, D.K. Jindal and R. Luxmi, Synth. Commun., 45, 1977 (2015); https://doi.org/10.1080/00397911.2015.1056796.
- C.P. Kaushik, K. Kumar, K. Lal and S.K. Singh, Chem. Biol. Interface, 4, 341 (2014).
- K. Lal, C.P. Kaushik and A. Kumar, Med. Chem. Res., 24, 3258 (2015); https://doi.org/10.1007/s00044-015-1378-9.
- M. Aufort, J. Herscovici, P. Bouhours, N. Moreau and C. Girard, Bioorg. Med. Chem. Lett., 18, 1195 (2008); https://doi.org/10.1016/j.bmcl.2007.11.111.
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- A. Cwiklicki and K. Rehse, Arch. Pharm. Pharm. Med. Chem., 337, 156 (2004); https://doi.org/10.1002/ardp.200300837.
- A. Mascarin, I.E. Valverde, S. Vomstein and T.L. Mindt, Bioconjug. Chem., 26, 2143 (2015); https://doi.org/10.1021/acs.bioconjchem.5b00444.
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- H. Nandivada, X. Jiang and J. Lahann, J. Adv. Mater., 19, 2197 (2007); https://doi.org/10.1002/adma.200602739.
- A.H. Banday, A.S. Shameem and B.A. Ganai, Org. Med. Chem. Lett., 13, 2191 (2012); https://doi.org/10.1186/2191-2858-2-13.
- R. Huisgen, G. Szeimies and L. Möbius, Chem. Ber., 100, 2494 (1967); https://doi.org/10.1002/cber.19671000806.
- H.C. Kolb, M.G. Finn and K.B. Sharpless, Angew. Chem. Int. Ed., 40, 2004 (2001); https://doi.org/10.1002/1521-3773(20010601)40:11<2004::AIDANIE2004>3.0.CO;2-5.
- C.W. Tornøe, C. Christensen and M. Meldal, J. Org. Chem., 67, 3057 (2002); https://doi.org/10.1021/jo011148j.
- C.P. Kaushik, K. Kumar, B. Narasimhan, D. Singh, P. Kumar and A. Pahwa, Monatsh. Chem., 148, 765 (2017); https://doi.org/10.1007/s00706-016-1766-y.
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References
M.K. Singh, M. Gangwar, D. Kumar, R. Tilak, G. Nath and A. Agarwal, Med. Chem. Res., 23, 4962 (2014); https://doi.org/10.1007/s00044-014-1063-4.
C.P. Kaushik, A. Pahwa, R. Thakur and P. Kaur, Synth. Commun., 47, 368 (2017); https://doi.org/10.1080/00397911.2016.1265983.
A. Ouahrouch, M. Taourirte, D. Schols, R. Snoeck, G. Andrei, J.W. Engels and H.B. Lazrek, Arch. Pharm. Chem. Life Sci., 348, 1 (2015); https://doi.org/10.1002/ardp.201500292.
B.K. Singh, A.K. Yadav, B. Kumar, A. Gaikwad, S.K. Sinha, V. Chaturvedi and R.P. Tripathi, Carbohydr. Res., 343, 1153 (2008); https://doi.org/10.1016/j.carres.2008.02.013.
K. Kumar, C. Biot, S. Carrère-Kremer, L. Kremer, Y. Guérardel, P. Roussel and V. Kumar, Organometallics, 32, 7386 (2013); https://doi.org/10.1021/om4009229.
J. de O. Santos, G.R. Pereira, G.C. Brandao, T.F. Borgati, L.M. Arantes, R.C. de Paula, L.F. Soares, M.F.A. do Nascimento, M.R.C. Ferreira, A.G. Taranto, F.P. Varottig and A.B. de Oliveira, J. Braz. Chem. Soc., 27, 551 (2016); https://doi.org/10.5935/0103-5053.20150287.
C.P. Kaushik, K. Kumar, K. Lal, B. Narasimhan and A. Kumar, Monatsh. Chem., 147, 817 (2016); https://doi.org/10.1007/s00706-015-1544-2.
C.P. Kaushik, K. Kumar, D. Singh, S.K. Singh, D.K. Jindal and R. Luxmi, Synth. Commun., 45, 1977 (2015); https://doi.org/10.1080/00397911.2015.1056796.
C.P. Kaushik, K. Kumar, K. Lal and S.K. Singh, Chem. Biol. Interface, 4, 341 (2014).
K. Lal, C.P. Kaushik and A. Kumar, Med. Chem. Res., 24, 3258 (2015); https://doi.org/10.1007/s00044-015-1378-9.
M. Aufort, J. Herscovici, P. Bouhours, N. Moreau and C. Girard, Bioorg. Med. Chem. Lett., 18, 1195 (2008); https://doi.org/10.1016/j.bmcl.2007.11.111.
M.H. Shaikh, D.D. Subhedar, B.B. Shingate, F.A. Kalam Khan, J.N. Sangshetti, V.M. Khedkar, L. Nawale, D. Sarkar, G.R. Navale and S.S. Shinde, Med. Chem. Res., 25, 790 (2016); https://doi.org/10.1007/s00044-016-1519-9.
P. Nagender, G. Malla Reddy, R. Naresh Kumar, Y. Poornachandra, C. Ganesh Kumar and B. Narsaiah, Bioorg. Med. Chem. Lett., 24, 2905 (2014); https://doi.org/10.1016/j.bmcl.2014.04.084.
W.T. Li, W.H. Wu, C.H. Tang, R. Tai and S.T. Chen, Comb. Sci, 13, 72 (2011); https://doi.org/10.1021/co1000234.
M. Whiting, J.C. Tripp, Y.C. Lin, W. Lindstrom, A.J. Olson, J.H. Elder, K.B. Sharpless and V.V. Fokin, J. Med. Chem., 49, 7697 (2006); https://doi.org/10.1021/jm060754+.
X. Ren, X. Pan, Z. Zhang, D. Wang, X. Lu, Y. Li, D. Wen, H. Long, J. Luo, Y. Feng, X. Zhuang, F. Zhang, J. Liu, F. Leng, X. Lang, Y. Bai, M. She, Z. Tu, J. Pan and K. Ding, J. Med. Chem., 56, 879 (2013); https://doi.org/10.1021/jm301581y.
A. Karakurt, M.D. Aytemir, J.P. Stables, M. Özalp, F. Betül Kaynak, S. Özbey and S. Dalkara, Arch. Pharm. Chem. Life Sci., 339, 513 (2006); https://doi.org/10.1002/ardp.200500248.
A. Cwiklicki and K. Rehse, Arch. Pharm. Pharm. Med. Chem., 337, 156 (2004); https://doi.org/10.1002/ardp.200300837.
A. Mascarin, I.E. Valverde, S. Vomstein and T.L. Mindt, Bioconjug. Chem., 26, 2143 (2015); https://doi.org/10.1021/acs.bioconjchem.5b00444.
M. van Dijk, K. Mustafa, A.C. Dechesne, C.F. van Nostrum, W.E. Hennink, D.T.S. Rijkers and R.M.J. Liskamp, Biomacromolecules, 8, 327 (2007); https://doi.org/10.1021/bm061010g.
H. Nandivada, X. Jiang and J. Lahann, J. Adv. Mater., 19, 2197 (2007); https://doi.org/10.1002/adma.200602739.
A.H. Banday, A.S. Shameem and B.A. Ganai, Org. Med. Chem. Lett., 13, 2191 (2012); https://doi.org/10.1186/2191-2858-2-13.
R. Huisgen, G. Szeimies and L. Möbius, Chem. Ber., 100, 2494 (1967); https://doi.org/10.1002/cber.19671000806.
H.C. Kolb, M.G. Finn and K.B. Sharpless, Angew. Chem. Int. Ed., 40, 2004 (2001); https://doi.org/10.1002/1521-3773(20010601)40:11<2004::AIDANIE2004>3.0.CO;2-5.
C.W. Tornøe, C. Christensen and M. Meldal, J. Org. Chem., 67, 3057 (2002); https://doi.org/10.1021/jo011148j.
C.P. Kaushik, K. Kumar, B. Narasimhan, D. Singh, P. Kumar and A. Pahwa, Monatsh. Chem., 148, 765 (2017); https://doi.org/10.1007/s00706-016-1766-y.
C.P. Kaushik, K. Kumar, S.K. Singh, D. Singh and S. Saini, Arab. J. Chem., 9, 865 (2016); https://doi.org/10.1016/j.arabjc.2013.09.023.