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Synthesis and Biological Evaluation of Naphthopyranopyrimidines Derivatives as Potential Antifungal and Antibacterial Activities
Corresponding Author(s) : Ramakoteswara Rao Chinta
Asian Journal of Chemistry,
Vol. 28 No. 4 (2016): Vol 28 Issue 4
Abstract
A new series of novel 8,10-dimethyl-12-aryl-12H-naphtho[1',2,5,6]pyrano[2,3-d]pyrimidine-9,11-diones derivatives synthesized from coupling (3CC) of aldehydes, b-naphthol and 1,3-dimethylbarbituric acid derivatives with using green condition through a simple, mild and efficient procedure utilizing cellulose sulfuric acid as a catalyst. Final compounds were evaluated for antibacterial and antifungal activity. Compounds 4a, 4d, 4h display high potent antifungal activity against Candida parapsilopsis, compound 4d show more potent activity (MIC 4.6 mg/mL) better than miconazole. While compound 4d most effective on bacterial against Micrococcus luteus, Staphylococcus aureus MTCC 96 and Staphylococcus aureus MTCC 2940 with (MIC 2.3 mg/mL).
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- A. Domling and I. Ugi, Angew. Chem. Int. Ed., 39, 3168 (2000); doi:10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U.
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- I. Ugi, Pure Appl. Chem., 73, 18 (2001); doi:10.1351/pac200173010187.
- R.R. Nagawade and D.B. Shinde, Acta Chim. Slov., 54, 642 (2007).
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- C. Kalinski, H. Lemoine, J. Schmidt, C. Burdack, J. Kolb, M. Umkehrer and G. Ross, Synthesis, 4007 (2008); doi:10.1055/s-0028-1083239.
- (a) G. Lewitt, US 4339267 (1983); Chem. Abstr.,98, 215602 (1983); (c) S. Senda, H. Fujimura, and H.J. Izumi, Patent 6824 (1969); Chem. Abstr.,70, 7800 (1969); (d) R. Wrigglesworth, W.D. Inglis, D.B. Livingstone, C. J. Snekling and H.C.S. Wood, J. Chem. Soc., Perkin Trans. I, 959 (1984); (e) C.N. O’Callaghan, M.L. Conalty, Proc. R. Ir. Acad. Sect. B, 83, 241 (1983).
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- (a) A. Shaabani and A. Maleki, Appl. Catal. A Gen., 331, 149 (2007); doi:10.1016/j.apcata.2007.07.021; (b) A. Shaabani, A. Maleki, J. Moghimi Rad and E. Soleimani, Chem. Pharm. Bull. (Tokyo), 55, 957 (2007); doi:10.1248/cpb.55.957; (c) J. Venu Madhav, Y. Thirupathi Reddy, P. Narsimha Reddy, M. Nikhil Reddy, S. Kuarm, P.A. Crooks and B. Rajitha, J. Mol. Catal. A: Chem., 304, 85 (2009); doi:10.1016/j.molcata.2009.01.028; (d) S. Ahmad, R. Abbas and B. Zahra, Catal. Commun., 9, 13 (2009); doi:10.1016/j.catcom.2007.05.021.
References
A. Domling and I. Ugi, Angew. Chem. Int. Ed., 39, 3168 (2000); doi:10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U.
J. Zhu and H. Bienayme, Multi-Component Reactions, Wiley-VCH, Weinheim (2005).
A. Domling, Chem. Rev., 106, 17 (2006); doi:10.1021/cr0505728.
I. Ugi, Pure Appl. Chem., 73, 18 (2001); doi:10.1351/pac200173010187.
R.R. Nagawade and D.B. Shinde, Acta Chim. Slov., 54, 642 (2007).
D.M. D’Souza and T.J.J. Mueller, Chem. Soc. Rev., 36, 1095 (2007); doi:10.1039/B608235C.
C.C.A. Cariou, G.J. Clarkson and M. Shipman, J. Org. Chem., 73, 9762 (2008); doi:10.1021/jo801664g.
C. Kalinski, H. Lemoine, J. Schmidt, C. Burdack, J. Kolb, M. Umkehrer and G. Ross, Synthesis, 4007 (2008); doi:10.1055/s-0028-1083239.
(a) G. Lewitt, US 4339267 (1983); Chem. Abstr.,98, 215602 (1983); (c) S. Senda, H. Fujimura, and H.J. Izumi, Patent 6824 (1969); Chem. Abstr.,70, 7800 (1969); (d) R. Wrigglesworth, W.D. Inglis, D.B. Livingstone, C. J. Snekling and H.C.S. Wood, J. Chem. Soc., Perkin Trans. I, 959 (1984); (e) C.N. O’Callaghan, M.L. Conalty, Proc. R. Ir. Acad. Sect. B, 83, 241 (1983).
(a) K.C. Joshi, R. Jain and K.J. Sharma, Indian Chem. Soc., 45, 202 (1988); (b) A.H.Bedair, H.A.Emam, N.A.El-Hady, K.A.R.Ahmed and A.M.El-Agrody, Farmaco, 56, 965 (2001); doi:10.1016/S0014-827X(01)01168-5.
D. Amsterdam, Susceptibility testing of antimicrobials in liquid media. in: V. Loman (Ed.), Antibiotics in Laboratory Medicine, fourth ed. Williams and Wilkins, Baltimore, MD, 52 (1996).
(a) T. Laitinen, A. Polvi, P. Rydman, J. Vendelin, V. Pulkkinen, P. Salmikangas, S. Mäkelä, M. Rehn, A. Pirskanen, A. Rautanen, M. Zucchelli, H. Gullstén, M. Leino, H. Alenius, T. Petäys, T. Haahtela, A. Laitinen, C. Laprise, T.J. Hudson and L.A. Laitinen, Science, 304, 300 (2004); doi:10.1126/science.1090010; (b) S.H. Mashraqui, M.B. Patil, H.D. Mistry, S. Ghadigaonkar and A. Meetsma, Chem. Lett., 33, 1058 (2004); doi:10.1246/cl.2004.1058; (c) J. Li, W. Tang, L. Lu and W. Su, Tetrahedron Lett., 49, 7117 (2008); doi:10.1016/j.tetlet.2008.09.129; (d) S. Gao, C.H. Tsai and C.F. Yao, Synlett, 949 (2009); (e) G.C. Nandi, S. Samai, R. Kumar and M.S. Singh, Tetrahedron, 65, 7129 (2009); doi:10.1016/j.tet.2009.06.024; (f) K. Praveen Kumar, S. Satyanarayana, P. Lakshmi Reddy, G. Narasimhulu, N. Ravirala and B.V. Subba Reddy, Tetrahedron Lett., 53, 1738 (2012); doi:10.1016/j.tetlet.2012.01.096.
(a) A. Shaabani and A. Maleki, Appl. Catal. A Gen., 331, 149 (2007); doi:10.1016/j.apcata.2007.07.021; (b) A. Shaabani, A. Maleki, J. Moghimi Rad and E. Soleimani, Chem. Pharm. Bull. (Tokyo), 55, 957 (2007); doi:10.1248/cpb.55.957; (c) J. Venu Madhav, Y. Thirupathi Reddy, P. Narsimha Reddy, M. Nikhil Reddy, S. Kuarm, P.A. Crooks and B. Rajitha, J. Mol. Catal. A: Chem., 304, 85 (2009); doi:10.1016/j.molcata.2009.01.028; (d) S. Ahmad, R. Abbas and B. Zahra, Catal. Commun., 9, 13 (2009); doi:10.1016/j.catcom.2007.05.021.