Synthesis and evaluation of new arylbenzo[b]thiophene and diarylthiophene derivatives as inhibitors of the NorA multidrug transporter of Staphylococcus aureus

van Bambeke, 2000, Biochem. Pharmacol., 60, 457, 10.1016/S0006-2952(00)00291-4 van Bambeke, 2003, J. Antimicrob. Chemother., 51, 1055, 10.1093/jac/dkg224 Li, 2004, Drugs, 64, 159, 10.2165/00003495-200464020-00004 McKeegan, 2004, Curr. Opin. Pharmacol., 4, 479, 10.1016/j.coph.2004.07.002 Nelson, 2002, Curr. Med. Chem. Anti Infect. Agents, 1, 35, 10.2174/1568012023355054 Lage, 2003, Int. J. Antimicrob. Agents, 22, 188, 10.1016/S0924-8579(03)00203-6 Ross, 1995, Mol. Microbiol., 4, 228 Reynolds, 2003, Int. J. Antimicrob. Agents, 22, 222, 10.1016/S0924-8579(03)00218-8 Lomovskaya, 2001, Curr. Med. Chem., 8, 1699, 10.2174/0929867013371743 Kaatz, 1993, Antimicrob. Agents Chemother., 37, 1086, 10.1128/AAC.37.5.1086 Neyfakh, 1993, Antimicrob. Agents Chemother., 37, 128, 10.1128/AAC.37.1.128 Renau, 1999, J. Med. Chem., 42, 4928, 10.1021/jm9904598 Renau, 2003, Biorg. Med. Chem. Lett., 13, 2755, 10.1016/S0960-894X(03)00556-0 Yoshida, 2006, Bioorg. Med. Chem., 14, 8506, 10.1016/j.bmc.2006.08.037 Markham, 1999, Antimicrob. Agents Chemother., 43, 2404, 10.1128/AAC.43.10.2404 Durette, P., Witzel, B. E., Rupprecht, K. M., Tiscler, A. N., Gallagher, T. F. US4663344, Merck & Co. Inc., 1987. Svoboda, 2000, Collect. Czech. Chem. Commun., 65, 1082, 10.1135/cccc20001082 Masaki, 2003, Bioorg. Med. Chem. Lett., 13, 4085, 10.1016/j.bmcl.2003.08.040 Boschelli, 1995, J. Med. Chem., 38, 4597, 10.1021/jm00022a026 Martinez-Esparza, 2001, J. Med. Chem., 44, 418, 10.1021/jm001059j Hrib, 1992, J. Med. Chem., 35, 2712, 10.1021/jm00092a024 De Nanteuil, 2003, Bioorg. Med. Chem. Lett., 13, 1705, 10.1016/S0960-894X(03)00233-6 Boulware, 2001, Antiviral Res., 51, 111, 10.1016/S0166-3542(01)00147-4 Mitsumori, 2003, J. Med. Chem., 46, 2446, 10.1021/jm0205189 Bettinetti, 2002, J. Med. Chem., 45, 4594, 10.1021/jm025558r Jones, 1984, J. Med. Chem., 27, 1057, 10.1021/jm00374a021 Palkowitz, 1997, J. Med. Chem., 40, 1407, 10.1021/jm970167b Pinney, 1999, Biorg. Med. Chem. Lett., 9, 1081, 10.1016/S0960-894X(99)00143-2 Chen, 2000, J. Org. Chem., 65, 8811, 10.1021/jo0004761 Gastpar, 1998, J. Med. Chem., 41, 4965, 10.1021/jm980228l Nishio, 1998, Helv. Chim. Acta, 81, 1207, 10.1002/hlca.19980810531 Okazawa, 2002, J. Am. Chem. Soc., 124, 5286, 10.1021/ja0259279 Penalva, 1999, Appl. Catal., A General, 182, 399, 10.1016/S0926-860X(99)00032-0 Lavenot, 1998, J. Organomet. Chem., 567, 49, 10.1016/S0022-328X(98)00667-6 Chandra, 2006, Bioorg. Med. Chem. Lett., 16, 1350, 10.1016/j.bmcl.2005.11.055 Ohta, 1990, Heterocycles, 11, 1951, 10.3987/COM-90-5467 Yokooji, 2004, Tetrahedron, 60, 6757, 10.1016/j.tet.2004.06.075 Glover, 2003, Org. Lett., 5, 301, 10.1021/ol027266q Masui, 2004, Org. Lett., 6, 2011, 10.1021/ol049386z Fournier Dit Chabert, 2002, Tetrahedron Lett., 43, 1829, 10.1016/S0040-4039(02)00128-4 Fournier Dit Chabert, 2004, Tetrahedron, 60, 3221, 10.1016/j.tet.2004.02.011 Pivsa-Art, 1998, Bull. Chem. Soc. Jpn., 71, 467, 10.1246/bcsj.71.467 Fournier Dit Chabert, 2006, Tetrahedron Lett., 47, 1015, 10.1016/j.tetlet.2005.11.108 De Dios, 2002, J. Med. Chem., 45, 4559, 10.1021/jm020901d Abreu, 2003, Tetrahedron Lett., 44, 6007, 10.1016/S0040-4039(03)01473-4 Wang, 2002, Tetrahedron, 58, 7365, 10.1016/S0040-4020(02)00588-4 Sasai, 1993, Tetrahedron Lett., 34, 855, 10.1016/0040-4039(93)89031-K Lygo, 2001, Tetrahedron, 57, 2403, 10.1016/S0040-4020(01)00094-1 Erlenmeyer, 1893, Ann. Chem., 1, 275 Neidlein, 1977, Arch. Pharm., 310, 635, 10.1002/ardp.19773100805 Fujita, 1983, Tetrahedron Lett., 24, 4573, 10.1016/S0040-4039(00)85959-6 Ojima, 1989, J. Org. Chem., 54, 4511, 10.1021/jo00280a014 Kumar, 1980, Synthesis, 836, 10.1055/s-1980-29228 Tegos, 2002, Antimicrob. Agents Chemother., 46, 3133, 10.1128/AAC.46.10.3133-3141.2002 Kaatz, 1995, Antimicrob. Agents Chemother., 39, 2650, 10.1128/AAC.39.12.2650 Lomovskaya, 2001, Antimicrob. Agents Chemother., 45, 105, 10.1128/AAC.45.1.105-116.2001 Gibbons, 2003, J. Antimicrob. Chemother., 51, 13, 10.1093/jac/dkg044 Daporta, 2004, Int. J. Antimicrob. Agents, 24, 185, 10.1016/j.ijantimicag.2004.01.012 Repolles Moliner, J., Pubill Coy, F., Cabeza Llorente, L., Carbo Banus, M., Cerda Riudavets, J., Negrie Rofes, C., Ferrer Siso, A. ES213020, Lacer S.A. 1999. Ahmed, 1995, J. Bacteriol., 177, 3904, 10.1128/jb.177.14.3904-3910.1995 Neyfakh, 1991, Proc. Natl. Acad. Sci. U.S.A., 88, 4781, 10.1073/pnas.88.11.4781 Denis, 1993, J. Antimicrob. Chemother., 32, 379, 10.1093/jac/32.3.379