Synthesis of Novel Substituted 4,6-Dimethoxy-N-phenyl-1,3,5-triazin-2-amine Derivatives and Their Antibacterial and Antifungal Activities

Ravindra S. Shinde; Shridhar D. Salunke

doi:10.14233/ajchem.2015.19114

Issue

Vol. 27 No. 11 (2015): Vol 27 Issue 11

Issue Published : July 16, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis of Novel Substituted 4,6-Dimethoxy-N-phenyl-1,3,5-triazin-2-amine Derivatives and Their Antibacterial and Antifungal Activities

https://doi.org/10.14233/ajchem.2015.19114

Ravindra S. Shinde

Research Center in Chemistry, Rajarshi Shahu Mahavidyalaya, Latur-413 512, India

Shridhar D. Salunke

Research Center in Chemistry, Rajarshi Shahu Mahavidyalaya, Latur-413 512, India

Corresponding Author(s) : Shridhar D. Salunke

salunke_shridhar@yahoo.co.in

Asian Journal of Chemistry, Vol. 27 No. 11 (2015): Vol 27 Issue 11
Article Published : July 16, 2015

Abstract

An efficient and convenient method of synthesis of 2-chloro-4,6-dimethoxy-1,3,5-triazine from cyanuric chloride in a short reaction time followed by synthesis of biological active novel substituted 4,6-dimethoxy-N-phenyl-1,3,5-triazin-2-amine (4a-x) using substituted anilines and heterocyclic amines, anhydrous K₂CO₃ in dry THF as solvent has been developed. Advantages of this methodology are short reaction time, excellent yield of products, easy work-up procedure. The synthesized compounds were confirmed by FT-IR, ¹H NMR, mass spectral data. All the synthesized derivatives (4a-x) were screened for their antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa species and antifungal activities against Candida albicans MTCC 227, Candida glabrata NCIM 3236, Candida tropicalis NCIM 3110 and Aspergillus niger NCIM 545 species.

Keywords

Antimicrobial Activity Cyanuric chloride Substituted 1 3 5-triazin-2-amine

S. Shinde, R., & D. Salunke, S. (2015). Synthesis of Novel Substituted 4,6-Dimethoxy-N-phenyl-1,3,5-triazin-2-amine Derivatives and Their Antibacterial and Antifungal Activities. Asian Journal of Chemistry, 27(11), 4130–4134. https://doi.org/10.14233/ajchem.2015.19114

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V.R. Avupati, R.P. Yejella, V.R. Parala, K.N. Killari, V.M.R. Papasani, P. Cheepurupalli, V.R. Gavalapu and B. Boddeda, Bioorg. Med. Chem. Lett., 23, 5968 (2013); doi:10.1016/j.bmcl.2013.08.063.

P. Dao, R. Jarray, J. Le Coq, D. Lietha, A. Loukaci, Y. Lepelletier, R. Hadj-Slimane, C. Garbay, F. Raynaud and H. Chen, Bioorg. Med. Chem. Lett., 23, 4552 (2013); doi:10.1016/j.bmcl.2013.06.038.

X. Chen, P. Zhan, C. Pannecouque, J. Balzarini, E. De Clercq and X. Liu, Eur. J. Med. Chem., 51, 60 (2012); doi:10.1016/j.ejmech.2012.02.019.

M.Y. Wani, A.R. Bhat, A. Azam, I. Choi and F. Athar, Eur. J. Med. Chem., 48, 313 (2012); doi:10.1016/j.ejmech.2011.12.033.

I. Sosič, B. Mirković, S. Turk, B. Štefane, J. Kos and S. Gobec, Eur. J. Med. Chem., 46, 4648 (2011); doi:10.1016/j.ejmech.2011.08.005.

G. Pastorin, S. Federico, S. Paoletta, M. Corradino, F. Cateni, B. Cacciari, K. Klotz, Z. Gao, K.A. Jacobson, G. Spalluto and S. Moro, Bioorg. Med. Chem., 18, 2524 (2010); doi:10.1016/j.bmc.2010.02.039.

M. Krecmerova, M. Masojidkova and A. Holy, Bioorg. Med. Chem., 18, 387 (2010); doi:10.1016/j.bmc.2009.10.044.

F. Popowycz, C. Schneider, S. DeBonis, D.A. Skoufias, F. Kozielski, C.M. Galmarini and B. Joseph, Bioorg. Med. Chem., 17, 3471 (2009); doi:10.1016/j.bmc.2009.03.007.

C. Zhou, J. Min, Z. Liu, A. Young, H. Deshazer, T. Gao, Y.T. Chang and N.R. Kallenbach, Bioorg. Med. Chem. Lett., 18, 1308 (2008); doi:10.1016/j.bmcl.2008.01.031.

N. Sunduru, A. Agarwal, S.B. Katiyar, Nishi, N. Goyal, S. Gupta and P.M.S. Chauhan, Bioorg. Med. Chem., 14, 7706 (2006); doi:10.1016/j.bmc.2006.08.009.

V. Garaj, L. Puccetti, G. Fasolis, J.-Y. Winum, J.-L. Montero, A. Scozzafava, D. Vullo, A. Innocenti and C.T. Supuran, Bioorg. Med. Chem. Lett., 15, 3102 (2005); doi:10.1016/j.bmcl.2005.04.056.

T. Vilaivan, N. Saesaengseerung, D. Jarprung, S. Kamchonwongpaisan, W. Sirawaraporn and Y. Yuthavong, Bioorg. Med. Chem., 11, 217 (2003); doi:10.1016/S0968-0896(02)00344-9.

M. Kitamura, F. Kawasaki, K. Ogawa, S. Nakanishi, H. Tanaka, K. Yamada and M. Kunishima, J. Org. Chem., 79, 3709 (2014); doi:10.1021/jo500376m.

A.B. Patel, K.H. Chikhalia and P. Kumari, Eur. J. Med. Chem., 79, 57 (2014); doi:10.1016/j.ejmech.2014.03.085.

R.V. Patel, P. Kumari, D.P. Rajani and K.H. Chikhalia, Eur. J. Med. Chem., 46, 4354 (2011); doi:10.1016/j.ejmech.2011.07.006.

B. Akhlaghinia and E.A. Roohi, Lett. Org. Chem., 2, 725 (2005); doi:10.2174/157017805774717571.

K. Bretterbauer and C. Schwarzinger, Curr. Org. Synth., 9, 342 (2012); doi:10.2174/157017912801270612.

G. Giacomelli, A. Porcheddu and L. De Luca, Curr. Org. Chem., 8, 1497 (2013); doi:10.2174/1385272043369845.

X. Qin, W. Lu, Y. Luo, G. Chang, A.M. Asiri, A.O. Al-Youbi and X. Sun, Curr. Nanosci., 8, 393 (2012); doi:10.2174/157341312800620340.

Issue

Vol. 27 No. 11 (2015): Vol 27 Issue 11

Synthesis of Novel Substituted 4,6-Dimethoxy-N-phenyl-1,3,5-triazin-2-amine Derivatives and Their Antibacterial and Antifungal Activities

Corresponding Author(s) : Shridhar D. Salunke

Abstract

Keywords

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