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Synthesis and Crystal Structure of Novel 9-Styrylquinoline Substituted Acridines as Potential Inhibitors of Bacteria
Corresponding Author(s) : Shu-An Li
Asian Journal of Chemistry,
Vol. 27 No. 2 (2015): Vol 27 Issue 2
Abstract
Novel compounds of 1,8-dioxodecahydroacridines were designed as potential inhibitors of bacteria and prepared via the multi-component reaction of styrylquinoline aldehydes, dimedone and ammonium acetate in high yield under mild condition. The structure of products has been characterized by X-ray crystal structural analyses, 1H NMR, IR, LC-MC and elemental analysis. The preliminary biological screening shows that target product display a certain degree of activity against the vibrio harveyi at 100 μg mL-1.
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- P. Shanmugasundaram, K.J. Prabahar and V.T. Ramakrishnan, J. Heterocycl. Chem., 30, 1003 (1993); doi:10.1002/jhet.5570300428.
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- T.J. Egan, D.C. Ross and P.A. Adams, FEBS Lett., 352, 54 (1994); doi:10.1016/0014-5793(94)00921-X.
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References
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P. Shanmugasundaram, P. Murugan, V.T. Ramakrishnan, N. Srividya and P. Ramamurthy, Heteroatom Chem., 7, 17 (1996); doi:10.1002/(SICI)1098-1071(199601)7:1<17::AID-HC3>3.0.CO;2-#.
P. Murugan, P. Shanmugasundaram, V.T. Ramakrishnan, N. Srividya, B. Venkatachalapathy, P. Ramamurthy, K. Gunasekaran and D. Velmurugan, J. Chem. Soc., Perkin Trans. II, 999 (1998), J. Chem. Soc., Perkin Trans. II, 999 (1998); doi:10.1039/a701401e.
P. Ilich, P.K. Mishra, S. Macura and T.P. Burghardt, Spectrochim. Acta A, 52, 1323 (1996); doi:10.1016/0584-8539(96)01719-9.
T.P. Burghardt and K. Ajtai, Biophys. Chem., 60, 119 (1996); doi:10.1016/0301-4622(96)00014-2.
V. Gekeler, R. Boer, W. Ise, K.H. Sanders, C. Schachtele and J. Beck, Biochem. Biophys. Res. Commun., 206, 119 (1995); doi:10.1006/bbrc.1995.1017.
R.G. Bretzel, C.C. Bollen, E. Maeser and K.F. Federlin, Am. J. Kidney Dis., 21, 53 (1993); doi:10.1016/0272-6386(93)70125-I.
V. Klusa, Drugs Future, 20, 135 (1995).
J. Avruch, N.C. Birnberg, J. Kyriakis, H. Liu and Q. Weng, Xanthene Compounds for Cancer Chemotherapy, WO 2004044219 A2 (2004).
A. Nakhi, P. Srinivas, M.S. Rahman, R. Kishore, G.P.K. Seerapu, K. Lalith Kumar, D. Haldar, M.V.B. Rao and M. Pal, Bioorg. Med. Chem. Lett., 23, 1828 (2013); doi:10.1016/j.bmcl.2013.01.026.
X.-M. Yu, F. Ramiandrasoa, L. Guetzoyan, B. Pradines, E. Quintino, D. Gadelle, P. Forterre, T. Cresteil, J.-P. Mahy and S. Pethe, ChemMedChem, 7, 587 (2012); doi:10.1002/cmdc.201100554.
X.H. Yang, P.H. Zhang, L.H. Hu, M. Zhang, C.-G. Liu, H.-J. Liu and Y.-H. Zhou, Ind. Crops Prod., 38, 14 (2012); doi:10.1016/j.indcrop.2011.12.035.
R. Boer and V. Gekeler, Drugs Future, 20, 499 (1995).
S. Chandrasekhar, Y. Srinivasa Rao, L. Sreelakshmi, B. Mahipal and C. Raji Reddy, Synthesis, 1737 (2008); doi:10.1055/s-2008-1067039.
X.S. Wang, D.S. Shi, S.H. Wang and S.J. Tu, Chinese J. Org. Chem., 23, 1291 (2003).
X.S. Wang, D.S. Shi, Y.F. Zhang and S.J. Tu, Chinese J. Org. Chem., 24, 430 (2004).
M. Dabiri, M. Baghbanzadeh and E. Arzroomchilar, Catal. Commun., 9, 939 (2008); doi:10.1016/j.catcom.2007.09.023.
X.S. Wang, M.M. Zhang, H. Jiang, D.-Q. Shi, S.-J. Tu, X.-Y. Wei and Z.-M. Zong, Synthesis, 4187 (2006); doi:10.1055/s-2006-950365.
T.S. Jin, J.S. Zhang, T.T. Guo, A.-Q. Wang and T.-S. Li, Synthesis, 2001 (2004); doi:10.1055/s-2004-829151.
N. Martín, M. Quinteiro, C. Seoane, J.L. Soto, A. Mora, M. Suárez, E. Ochoa, A. Morales and J.R.D. Bosque, Heterocycl. Chem., 32, 235 (1995); doi:10.1002/jhet.5570320139.
R. Wise, J.M. Andrews and L.J. Edwards, Antimicrob. Agents Chemother., 23, 559 (1983); doi:10.1128/AAC.23.4.559.
T.J. Egan, D.C. Ross and P.A. Adams, FEBS Lett., 352, 54 (1994); doi:10.1016/0014-5793(94)00921-X.
S.A. Jenekhe, L. Lu and M.M. Alam, Macromolecules, 34, 7315 (2001); doi:10.1021/ma0100448.
B.S. Reddy and A. Rivenson, Cancer Res., 53, 3914 (1993).
R. Musiol, J. Jampilek, V. Buchta, L. Silva, H. Niedbala, B. Podeszwa, A. Palka, K. Majerz-Maniecka, B. Oleksyn and J. Polanski, Bioorg. Med. Chem., 14, 3592 (2006); doi:10.1016/j.bmc.2006.01.016.
C.J. Frederickson, E.J. Kasarskis, D. Ringo and R.E. Frederickson, J. Neurosci. Methods, 20, 91 (1987); doi:10.1016/0165-0270(87)90042-2.
R. Musiol, J. Jampilek, K. Kralova, D.R. Richardson, D. Kalinowski, B. Podeszwa, J. Finster, H. Niedbala, A. Palka and J. Polanski, Bioorg. Med. Chem., 15, 1280 (2007); doi:10.1016/j.bmc.2006.11.020.
R. Musiol, J. Jampilek, V. Buchta, L. Silva, H. Niedbala, B. Podeszwa, A. Palka, K. Majerz-Maniecka, B. Oleksyn and J. Polanski, Bioorg. Med. Chem., 14, 3592 (2006); doi:10.1016/j.bmc.2006.01.016.
A. Merschaert, P. Boquel, J.P. Van Hoeck, H. Gorissen, A. Borghese, B. Bonnier, A. Mockel and F. Napora, Org. Process Res. Dev., 10, 776 (2006); doi:10.1021/op060036x.
Z.-M. Zhang, S.-A. Li, L.-P. Wang, Q. Dong and J.K. Liang, Chinese J. Pharmaceuticals, 41, 92 (2010).
H.T. Hsien and M.H. David, Process for 3-(2-(7-chloro-2-quinolinyl)ethenyl)- benzaldehyde, US Patent 5869673 (1999).
D.M. Hobbs, P. Schubert and H.H. Tung, Ind. Eng. Chem. Res., 36, 5302 (1997); doi:10.1021/ie970438g.
J. Gilmore and A. Todd, N-Benzyl-indoles, Processes for their Preparation and Pharmaceutical Compositions Containing them: European Patent, 469833; Chem. Abstr., 116, 214508 (1992).
G.M. Sheldrick, SHELX-97, Program for the Solution and Refinement of Crystal Structures, University of Göttingen, Germany (1997).
X. Wang, B.F. Chu, C.L. Wang et al., Clin. Stomatol., 20, 662 (2004).