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Design and New Synthetic Approach of Indole Based 1,2,3-Triazoles: A Potent Antimicrobial Agents
Corresponding Author(s) : Dodla Srinivasa Reddy
Asian Journal of Chemistry,
Vol. 29 No. 3 (2017): Vol 29 Issue 3
Abstract
A series of novel 5-methyl-1-(1-methyl-1H-indol-3-ylmethyl)-1H-[1,2,3]triazole-4-carboxylic acid phenylamides (6a-f) have been synthesized in good to excellent yields by treating 5-methyl-1-(1-methyl-1H-indol-3-ylmethyl)-1H-[1,2,3]triazole-4-carbonyl chloride (5) with different aromatic amines. To get the target compounds, the initial intermediate, 1-methyl-1H-indol-3-yl-methyldiazonium chloride (2) was achieved from the raw material, 1-methyl-1H-indol-3-yl-methylamine (1) through diazotization. Further compound, 1-methyl-1H-indol-3-yl-methylazide (3) was prepared from the reaction between compound 2 and sodium azide. Additionally, intermediate 3 is turned into 5-methyl-1-(1-methyl-1H-indol-3-ylmethyl)-1H-[1,2,3]triazole-4-carboxylic acid (4) with ethyl acetoacetate. Finally, the last intermediate, 5-methyl-1-(1-methyl-1H-indol-3-ylmethyl)-1H-[1,2,3]triazole-4-carbonyl chloride (5) was obtained from the reaction between compound 4 and thionyl chloride. The chemical structures of the all newly synthesized compounds were elucidated by their IR, 1H and 13C NMR, mass spectral data and elemental analysis. The target compounds were used to find their antimicrobial activity against various microorganisms. According to the screening results, compounds 6a, 6c, 6d and 6f and showed significant antibacterial activity and compounds 6d and 6e performed remarkable antifungal activity.
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References
K.K. Kumar, S.P. Seenivasan, V. Kumar and T.M. Das, Carbohydr. Res., 346, 2084 (2011).
N. Pokhodylo, O. Shyyka and V. Matiychuk, Med. Chem. Res., 23, 2426 (2014)
N.G. Aher, V.S. Pore, N.N. Mishra, A. Kumar, P.K. Shukla, A. Sharma and M.K. Bhat, Bioorg. Med. Chem. Lett., 19, 759 (2009).
N. Boechat, L.C.S. Pinheiro, O.A. Santos-Filho and I.C. Silva, Molecules, 16, 8083 (2011).
P. Coghi, N. Vaiana, M.G. Pezzano, L. Rizzi, M. Kaiser, R. Brun and S. Romeo, Bioorg. Med. Chem. Lett., 18, 4658 (2008).
K. El Akri, K. Bougrin, J. Balzarini, A. Faraj and R. Benhida, Bioorg. Med. Chem. Lett., 17, 6656 (2007).
M.L. Ferreira, M.V.N. Souza, S.M.S.V. Wardell, J.L. Wardell, T.R.A. Vasconcelos, V.F. Ferreira and M.C.S. Lourenço, J. Carbohydr. Chem., 29, 265 (2010).
A.K. Jordão, P.P. Afonso, V.F. Ferreira, M.C.B.V. de Souza, M.C.B. Almeida, C.O. Beltrame, D.P. Paiva, S.M.S.V. Wardell, J.L. Wardell, E.R.T. Tiekink, C.R. Damaso and A.C. Cunha, Eur. J. Med. Chem., 44, 3777 (2009).
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E.N. Silva Jr., M.A.B.F. Moura, A.V. Pinto, M.C.F.R. Pinto, M.C.B.V. Souza, A.J. Araújo, C. Pessoa, L.V. Costa-Lotufo, R.C. Montenegro, M.O. Moraes, V.F. Ferreira and M.O.F. Goulart, J. Braz. Chem. Soc., 20, 635 (2009).
T.A. Kirschberg, M. Balakrishnan, W. Huang, R. Hluhanich, N. Kutty, A.C. Liclican, D.J. McColl, N.H. Squires and E.B. Lansdon, Bioorg. Med. Chem. Lett., 18, 1131 (2008).
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Z. Liu, L. Tang, H. Zhu, T. Xu, C. Qiu, S. Zheng, Y. Gu, J. Feng, Y. Zhang and G. Liang, J. Med. Chem., 59, 4637 (2016).
A.S. Salman, N.A. Mahmoud, A. Abdel-Aziem, M.A. Mohamed and D.M. Elsisi, Int. J. Org. Chem., 5, 81 (2015).
M.C. Koksal-Akkoc and Y.Y. Mine, Turk. J. Chem., 36, 515 (2012).
A.R. Saundane, K. Rudresh, N.D. Satyanarayan and S.P. Hiremath, Indian J. Pharm. Sci., 60, 379 (1998).