Synthesis, Anti-bacterial and Anti-fungal evaluation of 3-(Substitutedphenyl)-N-(4H-1,2,4-triazol-4 yl)acrylamide
Subject Areas : Journal of the Iranian Chemical ResearchPravinkumar M. Patel 1 , Ashvin D. Panchal 2
1 - Industrial Chemistry Department, Science College, Vallabh Vidyangar, Gujarat, India
2 - Industrial Chemistry Department, Science College, Vallabh Vidyangar, Gujarat, India
Keywords: Antifungal, Antibacterial, triazole, Chalcone,
Abstract :
The Series of 3-(Substitutedphenyl)-N-(4H-1,2,4-triazol-4-yl)acrylamide compounds were prepared byreaction of 4-amino-1,2,4-Triazole with Acetyl Chloride followed by Claisen-Schmidt Condensation reactionwith different aromatic aldehydes. The structures of new compounds were confirmed by IR, 1H-NMR and13C-NMR spectral data. Anti-bacterial and Anti-fungal activities were evaluated and compared with thestandard drugs, some compounds of the series exhibited promising anti-microbial and anti-fungal activitycompared to standard drugs.
[1] N.D. Heindel, J.R. Reid, J. Heterocycl. Chem. 17 (1980) 1087-1088.
[2] B.S. Holla, B. Kalluraya, K.R. Sridhar, E. Drake, L.M. Thomas, K.K. Bhandary, M.S. Levine, Eur. J.
Med. Chem. 29 (1994) 301-308.
[3] V. Mathew, J. Keshavayya, V.P. Vidya, Acharya, B.M. Reddy, Eur. J. Med. Chem. 41, (2006) 1048-
1058.
[4] The Merck Index, Merck Co. Inc., twelfth ed., USA. 1996.
[5] J. Haber, Cas. Lek. Cesk. 140 (2001) 596-604.
[6] A. Brucato, A. Coppola, S. Gianguzza, P.M. Provenzano, Boll. Soc. Ital. Biol. Sper. 54 (1978) 1051-
1057.
[7] D.L. Coffen, R.I. Fryer, U.S. Patent: 3,849,434, 1974, Chem. Abstr. 85 (1975) 73044.
[8] M. Shiroki, T. Tahara, K. Araki Jap. Patent, 75100096, 1975, Chem. Abstr. 84 (1976) 59588.
[9] F.D. Povelitsa, A.G. Gural, Antibiotiki Moscow 18,1973,71, Chem. Abstr. 78 (1973) 93044.
[10] H.M. Yang, H.R. Shin, S.H. Cho, S.C. Bang, G.Y. Song, J.H. Ju, Bioorg. Med. Chem. 15 (2007) 104-
111.
[11] L. Svetaz, A. Tapia, S.N. Lopez, R.L.E. Furlan, E. Petenatt, R. Pioli, J. Agric. Food. Chem. 52 (2004)
3297-3300.
[12] M. Sortino, P. Delgado, S. Juarez, J. Quiroga, R. Abonia, B. Insuasty, Bioorg. Med. Chem. 15 (2007)
484-494.
[13] J.N. Dominguez, C. Leon, J. Rodrigues, J. Gut, P.J. Rosenthal, J. Med. Chem. 48 (2005) 3654-3658.
[14] A. Valla, B. Valla, D. Cartier, R.L. Guillou, R. Labia, L. Florent, Eur. J. Med. Chem. 41 (2006) 142-
146.
[15] W.D. Seo, Y.B. Ryu, M.J. Curtis-Long, C.W. Lee, H.W. Ryu, K.C. Jang, Eur. J. Med. Chem. 45 (2010)
2010-2017.
[16] A.L. Barry, In A. L. Barry (ed.), Lea & Febiger Philadelphia, 1976.
[17] K.E. Cooper, Analytical microbiology II, In F. Kavanagh (ed.), Academic Press Inc. New York, 1972.
[18] M.F. Mallette, J.R. Norris, D.W. Ribbons, Methods in Microbiology, Academic Press, London, 1969.