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Design, Synthesis and Biological Evaluation of Thiophene Based Pyrimidin-4-one Derivatives as New Type of Antimicrobial Agents
Corresponding Author(s) : D. Ramachandran
Asian Journal of Chemistry,
Vol. 28 No. 9 (2016): Vol 28 Issue 9
Abstract
In the present investigation, a novel series of 3-(benzylidene-amino)-2-methyl-5-phenyl-3H-thieno [2,3-d]pyrimidin-4-one and its derivatives (5a-i) were synthesized by condensation reaction from the final intermediate, 3-amino-2-methyl-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one (4). The synthesis of the title compounds commenced from commercially available 2-amino-4-phenyl-thiophene-3-carboxylic acid ethyl ester (1) and by involving 2-amino-4-phenyl-thiophene-3-carboxylic acid (2) and 2-methyl-5-phenyl-thieno[2,3-d][1,3]oxazin-4-one (3) as reactive intermediates. The chemical structures of synthesized compounds were characterized by IR, 1H NMR, mass spectral data and elemental analysis. The final compounds were used to screen for their antifungal activity against two strains of fungi.
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- A. Kamal, D. Dastagiri, M.J. Ramaiah, J.S. Reddy, E.V. Bharathi, M.K. Reddy, M.V.P. Sagar, T.L. Reddy, S.N.C.V.L. Pushpavalli and M. Pal-Bhadra, Eur. J. Med. Chem., 46, 5817 (2011); doi:10.1016/j.ejmech.2011.09.039.
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- M.B. Deshmukh, S.M. Salunkhe, D.R. Patil and P.V. Anbhule, Eur. J. Med. Chem., 44, 2651 (2009); doi:10.1016/j.ejmech.2008.10.018.
- A.R. Gholap, K.S. Toti, F. Shirazi, M.V. Deshpande and K.V. Srinivasan, Tetrahedron, 64, 10214 (2008); doi:10.1016/j.tet.2008.08.033.
- O. McCarthy, A. Musso-Buendia, M. Kaiser, R. Brun, L.M. Ruiz-Perez, N.G. Johansson, D.G. Pacanowska and I.H. Gilbert, Eur. J. Med. Chem., 44, 678 (2009); doi:10.1016/j.ejmech.2008.05.018.
- K.M. Amin, F.M. Awadalla, A.A.M. Eissa, S.M. Abou-Seri and G.S. Hassan, Bioorg. Med. Chem., 19, 6087 (2011); doi:10.1016/j.bmc.2011.08.037.
- S.A. Rahaman, Y. Rajendra Pasad, P. Kumar and B. Kumar, Saudi Pharm. J., 17, 255 (2009); doi:10.1016/j.jsps.2009.08.001.
- E.P.S. Falcao, 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.
- R.J. Gillespie, S.J. Bamford, A. Clay, S. Gaur, T. Haymes, P.S. Jackson, A.M. Jordan, B. Klenke, S. Leonardi, J. Liu, H.L. Mansell, S. Ng, M. Saadi, H. Simmonite, G.C. Stratton, R.S. Todd, D.S. Williamson and I.A. Yule, Bioorg. Med. Chem., 17, 6590 (2009); doi:10.1016/j.bmc.2009.07.078.
- National Committee for Clinical Laboratory Standards (NCCLs), Standard Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria, Which Grows Aerobically, Nat. Comm. Lab. Standards, Villanova, pp 242 (1982).
References
A. Kamal, D. Dastagiri, M.J. Ramaiah, J.S. Reddy, E.V. Bharathi, M.K. Reddy, M.V.P. Sagar, T.L. Reddy, S.N.C.V.L. Pushpavalli and M. Pal-Bhadra, Eur. J. Med. Chem., 46, 5817 (2011); doi:10.1016/j.ejmech.2011.09.039.
V. Summa, A. Petrocchi, F. Bonelli, B. Crescenzi, M. Donghi, M. Ferrara, F. Fiore, C. Gardelli, O. Gonzalez Paz, D.J. Hazuda, P. Jones, O. Kinzel, R. Laufer, E. Monteagudo, E. Muraglia, E. Nizi, F. Orvieto, P. Pace, G. Pescatore, R. Scarpelli, K. Stillmock, M.V. Witmer and M. Rowley, J. Med. Chem., 51, 5843 (2008); doi:10.1021/jm800245z.
M.B. Deshmukh, S.M. Salunkhe, D.R. Patil and P.V. Anbhule, Eur. J. Med. Chem., 44, 2651 (2009); doi:10.1016/j.ejmech.2008.10.018.
A.R. Gholap, K.S. Toti, F. Shirazi, M.V. Deshpande and K.V. Srinivasan, Tetrahedron, 64, 10214 (2008); doi:10.1016/j.tet.2008.08.033.
O. McCarthy, A. Musso-Buendia, M. Kaiser, R. Brun, L.M. Ruiz-Perez, N.G. Johansson, D.G. Pacanowska and I.H. Gilbert, Eur. J. Med. Chem., 44, 678 (2009); doi:10.1016/j.ejmech.2008.05.018.
K.M. Amin, F.M. Awadalla, A.A.M. Eissa, S.M. Abou-Seri and G.S. Hassan, Bioorg. Med. Chem., 19, 6087 (2011); doi:10.1016/j.bmc.2011.08.037.
S.A. Rahaman, Y. Rajendra Pasad, P. Kumar and B. Kumar, Saudi Pharm. J., 17, 255 (2009); doi:10.1016/j.jsps.2009.08.001.
E.P.S. Falcao, 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.
R.J. Gillespie, S.J. Bamford, A. Clay, S. Gaur, T. Haymes, P.S. Jackson, A.M. Jordan, B. Klenke, S. Leonardi, J. Liu, H.L. Mansell, S. Ng, M. Saadi, H. Simmonite, G.C. Stratton, R.S. Todd, D.S. Williamson and I.A. Yule, Bioorg. Med. Chem., 17, 6590 (2009); doi:10.1016/j.bmc.2009.07.078.
National Committee for Clinical Laboratory Standards (NCCLs), Standard Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria, Which Grows Aerobically, Nat. Comm. Lab. Standards, Villanova, pp 242 (1982).