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Synthesis and Characterization of Novel Pyridine and Pyrimidine Based 1,2,4-Triazoles with Nematicidal Activity
Corresponding Author(s) : B. Satyanarayana Reddy
Asian Journal of Chemistry,
Vol. 28 No. 2 (2016): Vol 28 Issue 2
Abstract
A series of new 2-phenyl-pyrido[2,3-e]-[1,2,4]triazolo[1,5-c]pyrimidine and its derivatives (5a-f) have been synthesized conveniently by cyclization of N-(4-imino-4H-pyrido[2,3-d]pyrimidin-3-yl)-benzamide and its derivatives (4a-f). The synthesis of title compounds commenced from commercially obtainable 2-amino-3-cyanopyridine (1) and by including N-(3-cyano-pyridin-2-yl)-formimidic acid ethyl ester (2) and benzoic acid N’-[(3-cyano-pyridin-2-ylimino)-methyl]hydrazide and its derivatives (3a-f) as intermediates. The chemical structures of all newly discovered compounds were established by IR, 1H NMR and 13C NMR, mass spectral data and elemental analysis. Further, the target compounds have been used to find their nematicidal activity towards two well known nematicides such as Ditylenchus myceliophagus and Caenorhabditis elegans.
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- F. Foroumadi, S. Mansouri, Z. Kiani and A. Rahmani, Eur. J. Med. Chem., 38, 851 (2003); doi:10.1016/S0223-5234(03)00148-X.
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- S.A. Rahaman, Y.R. Pasad, P. Kumar and B. Kumar, Saudi Pharm. J., 17, 255 (2009); doi:10.1016/j.jsps.2009.08.001.
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- C.W. McBeth and G.B. Bergeson, Phytopathology, 43, 264 (1953).
References
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S. Rollas, N. Kalyoncuoglu, D. Sur-Altiner and Y. Yegenoglu, Pharmazie, 48, 308 (1993).
I. Mir, M.T. Siddiqui and A. Comrie, Tetrahedron, 26, 5235 (1970); doi:10.1016/S0040-4020(01)98732-0.
W. Rudnicka, H. Foks, M. Janowiec and Z. Zwolska-Kwiek, Acta Pol. Pharm., 43, 523 (1986).
B.S. Holla, K.V. Malini, B.S. Rao, B.K. Sarojini and N.S. Kumari, Eur. J. Med. Chem., 38, 313 (2003); doi:10.1016/S0223-5234(02)01447-2.
H.L. Yale and L.J. Piala, J. Med. Chem., 9, 42 (1966); doi:10.1021/jm00319a010.
M.Y. Mhasalkar, M.H. Shah, S.T. Nikam, K.G. Anantanarayanan and C.V. Deliwala, J. Med. Chem., 13, 672 (1970); doi:10.1021/jm00298a021.
V.M. Reddy and K.R. Reddy, Chem. Pharm. Bull. (Tokyo), 58, 953 (2010); doi:10.1248/cpb.58.953.
Z.A. Kaplancikli, G.T. Zitouni, G. Revial and K. Guven, Arch. Pharm. Res., 27, 1081 (2004); doi:10.1007/BF02975108.
M.S. Al-Saadi, H.M. Faidallah and S.A.F. Rostom, Arch. Pharm. Chem. Life Sci., 341, 424 (2008); doi:10.1002/ardp.200800026.
K.D. Tripathi, Essentials of Medical Pharmacology, Jaypee Brothers, New Delhi, edn 5, pp. 627 (2004).
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K. Rehse and T. Baselt, Arch. Pharmazie, 341, 645 (2008); doi:10.1002/ardp.200700046.
H.N. Karade, B.N. Acharya, M. Sathe and M.P. Kaushik, Med. Chem. Res., 17, 19 (2008); doi:10.1007/s00044-008-9089-0.
R.N. Sharma, F.P. Xavier, K.K. Vasu, S.C. Chaturvedi and S.S. Pancholi, J. Enzyme Inhib. Med. Chem., 24, 890 (2009); doi:10.1080/14756360802519558.
K. Karimain, Exp. Opin. Ther. Pat., 19, 369 (2009); doi:10.1517/13543770802683066.
A. Kamal, D. Dastagiri, M.J. Ramaiah, J.S. Reddy, E.V. Bharathi, M.K. Reddy, M.V. Prem Sagar, T.L. Reddy, S.N.C.V.L. Pushpavalli and M. Bhandra, Eur. J. Med. Chem., 46, 5817 (2011); doi:10.1016/j.ejmech.2011.09.039.
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E.P.S. Falcão, S.J. de Melo, R.M. Srivastava, M.T.J.A. Catanho and S.C. Do Nascimento, Eur. J. Med. Chem., 41, 276 (2006); doi:10.1016/j.ejmech.2005.09.009.
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