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Synthesis and Antibacterial Activity of Substituted Quinoline Derivatives
Corresponding Author(s) : Alka Rani
Asian Journal of Chemistry,
Vol. 28 No. 9 (2016): Vol 28 Issue 9
Abstract
An efficient and convenient method is reported for the synthesis of various substituted quinolines through the condensation of o-amino aryl carbonyls with ketones containing an active methylene group in the presence of CuSO4·5H2O as catalyst at room temperature to yeild substituted quinolines (3a-l). All the synthesized compounds were fully characterized and screened for their antibacterial activities.
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- R.D. Larsen, E.G. Corley, A.O. King, J.D. Carroll, P. Davis, T.R. Verhoeven, P.J. Reider, M. Labelle, J.Y. Gauthier, Y.B. Xiang and R.J. Zamboni, J. Org. Chem., 61, 3398 (1996); doi:10.1021/jo952103j.
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- T.Asao, S. Okazaki, S. Wakita, T. Utsuki and Y. Yamada, JP, 09143166, A2 (1997).
- A.L. Barry, The Antimicrobic Susceptibility Test: Principles and Practices; Lea and Febiger: Philadelphia, p. 180 (1976).
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References
R.D. Larsen, E.G. Corley, A.O. King, J.D. Carroll, P. Davis, T.R. Verhoeven, P.J. Reider, M. Labelle, J.Y. Gauthier, Y.B. Xiang and R.J. Zamboni, J. Org. Chem., 61, 3398 (1996); doi:10.1021/jo952103j.
(a) G. Roma, M. Di Braccio, G. Grossi, F. Mattioli and M. Ghia, Eur. J. Med. Chem., 35, 1021 (2000); doi:10.1016/S0223-5234(00)01175-2; (b) J.P. Michael, Nat. Prod. Rep., 14, 605 (1997); doi:10.1039/np9971400605; (c) Y.L. Chen, K.C. Fang, J.Y. Sheu, S.L. Hsu and C.C. Tzeng, J. Med. Chem., 44, 2374 (2001); doi:10.1021/jm0100335.
(a) B. Kalluraya and S. Sreenivasa, Farmaco, 53, 399 (1998); doi:10.1016/S0014-827X(98)00037-8; (b) D. Dubé, M. Blouin, C. Brideau, C.-C. Chan, S. Desmarais, D. Ethier, J.-P. Falgueyret, R.W. Friesen, M. Girard, Y. Girard, J. Guay, D. Riendeau, P. Tagari and R.N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998); doi:10.1016/S0960-894X(98)00201-7; (c) M.P. Maguire, K.R. Sheets, K. McVety, A.P. Spada and A. Zilberstein, J. Med. Chem., 37, 2129 (1994); doi:10.1021/jm00040a003.
(4) T. Eicher and S. Hauptmann, The Chemistry of Heterocycles, pp. 316-336 (2003).
(a) H. Ginsburg and M. Krugliak, Biochem. Pharmacol., 43, 63 (1992); doi:10.1016/0006-2952(92)90662-3; (b) M. Foley and L. Tilley, Int. J. Parasitol., 27, 231 (1997); doi:10.1016/S0020-7519(96)00152-X; (c) M.Foley, Pharmacol. Ther., 79, 55 (1998); doi:10.1016/S0163-7258(98)00012-6; (d) P.M. O'Neill, P.G. Bray, S.R. Hawley, S.A. Ward and B.K. Park, Pharmacol. Ther., 77, 29 (1998); doi:10.1016/S0163-7258(97)00084-3; (e) C.D.Fitch, Life Sci., 74, 1957 (2004); doi:10.1016/j.lfs.2003.10.003.
(a) J.P. Michael, Nat. Prod. Rep., 25, 166 (2008); doi:10.1039/B612168N; (b) J.P. Michael, Nat. Prod. Rep., 24, 223 (2007); doi:10.1039/b509528j; (c) S.B. Mhaske and N.P. Argade, Tetrahedron, 62, 9787 (2006); doi:10.1016/j.tet.2006.07.098; (d) D.J. Connolly, D. Cusack, T.P. O'Sullivan and P.J. Guiry, Tetrahedron, 61, 10153 (2005); doi:10.1016/j.tet.2005.07.010.
T. Nomura, Z.-Z. Ma, Y. Hano and Y.-J. Chen, Heterocycles, 46, 541 (1997); doi:10.3987/COM-97-S65.
A. Cagir, S.H. Jones, R. Gao, B.M. Eisenhauer and S.M. Hecht, J. Am. Chem. Soc., 125, 13628 (2003); doi:10.1021/ja0368857.
T. Efferth, Y.-J. Fu, Y.-G. Zu, G. Schwarz, V.-S. Konkimalla and M. Wink, Curr. Med. Chem., 14, 2024 (2007); doi:10.2174/092986707781368441.
(a) T.G. Burke and Z.H.J. Mi, Med. Chem., 37, 40 (1994); doi:10.1021/jm00027a005; (b) B.M. Fox, X. Xiao, S. Antony, G. Kohlhagen, Y. Pommier, B.L. Staker, L. Stewart and M. Cushman, J. Med. Chem., 46, 3275 (2003); doi:10.1021/jm0300476.
(a) T. Utsugi, K. Aoyagi, T. Asao, S. Okazaki, Y. Aoyagi, M. Sano, K. Wierzba and Y. Yamada, Jpn. J. Cancer Res., 88, 992 (1997); doi:10.1111/j.1349-7006.1997.tb00320.x; (b) Y. Aoyagi, T. Kobunai, T. Utsugi, T. Oh-hara and Y. Yamada, Jpn. J. Cancer Res., 90, 578 (1999); doi:10.1111/j.1349-7006.1999.tb00786.x; (c) K. Ishida and T. Asao, Biochim. Biophys. Acta, 1587, 155 (2002); doi:10.1016/S0925-4439(02)00078-9.
(a) G. Kohlhagen, K. Paull, M. Ciishman, P. Nagafuji and Y. Pommier, Mol. Pharmacol., 54, 50 (1998); doi:10.1124/mol.54.1.50; (b) S. Antony, M. Jayaraman, G. Laco, G. Kohlhagen, K.W. Kohn, M. Cushman and Y. Pommier, Cancer Res., 63, 7428 (2003).
(a) M. Cushman, M. Jayaraman, J.A. Vroman, A.K. Fukunaga, B.M. Fox, G. Kohlhagen, D. Strumberg and Y. Pommier, J. Med. Chem., 43, 3688 (2000); doi:10.1021/jm000029d; (b) M. Jayaraman, B.M. Fox, M. Hollingshead, G. Kohlhagen, Y. Pommier and M. Cushman, J. Med. Chem., 45, 242 (2002); doi:10.1021/jm000498f; (c) M. Nagarajan, X. Xiao, S. Antony, G. Kohlhagen, Y. Pommier and M.J. Cushman, Med. Chem., 46, 5712 (2003); doi:10.1021/jm030313f; (d) B.L. Staker, M.D. Feese, M. Cushman, Y. Pommier, D. Zembower, L. Stewart and A.B. Burgin, J. Med. Chem., 48, 2336 (2005); doi:10.1021/jm049146p.
(a) Y.H. Hsiang, R. Hertzberg, S. Hecht and L.F. Liu, J. Biol. Chem., 260, 14873 (1985); (b) R.P. Hertzberg, M.J. Caranfa and S.M. Hecht, Biochemistry, 28, 4629 (1989); doi:10.1021/bi00437a018; (c) L. Stewart, M.R. Redinbo, X. Qiu, W.G. Hoi and J.J. Champoux, Science, 279, 1534 (1998); doi:10.1126/science.279.5356.1534.
T.Asao, S. Okazaki, S. Wakita, T. Utsuki and Y. Yamada, JP, 09143166, A2 (1997).
A.L. Barry, The Antimicrobic Susceptibility Test: Principles and Practices; Lea and Febiger: Philadelphia, p. 180 (1976).
P.M. Reddy, Y.P. Ho, K. Shanker, R. Rohini and V. Ravinder, Eur. J. Med. Chem., 44, 2621 (2009); doi:10.1016/j.ejmech.2008.09.035.