Mechanism and synthesis of pharmacologically active quinolones from Morita–Baylis–Hillman adducts

Tetrahedron - Tập 66 - Trang 4370-4376 - 2010
Giovanni W. Amarante1, Mario Benassi2, Robert N. Pascoal1, Marcos N. Eberlin2, Fernando Coelho1
1Laboratory of Natural Products and Drug Synthesis, University of Campinas, Institute of Chemistry, 13083-970, Campinas, São Paulo, Brazil
2ThoMSon Mass Spectrometry Laboratory, University of Campinas, Institute of Chemistry, 13083-970, Campinas, São Paulo, Brazil

Tài liệu tham khảo

Lescher, 1962, J. Med. Pharm. Chem., 5, 1063, 10.1021/jm01240a021 Emmerson, 2003, J. Antimicrob. Chemother., 51, 13, 10.1093/jac/dkg208 Wise, 1984, J. Antimicrob. Chemother., 13, 59, 10.1093/jac/13.suppl_B.59 Naber, 1996, Chemotherapy, 42, 1, 10.1159/000239485 Balfour, 1995, Drugs, 49, 794, 10.2165/00003495-199549050-00010 Jones, 2000, Clin. Infect. Dis., 31, 16, 10.1086/314054 Blondeau, 1999, J. Antimicrob. Chemother., 43, 1, 10.1093/jac/43.suppl_2.1 Crumplin, 1976, Nature, 260, 643, 10.1038/260643a0 Gellert, 1976, Proc. Natl. Acad. Sci. U.S.A., 73, 3872, 10.1073/pnas.73.11.3872 Wang, 1985, Annu. Rev. Biochem., 54, 665, 10.1146/annurev.bi.54.070185.003313 Gootz, 1996, Med. Res. Rev., 16, 433, 10.1002/(SICI)1098-1128(199609)16:5<433::AID-MED3>3.0.CO;2-W Drlica, 1997, Microbiol. Mol. Biology Rev., 61, 377 Zhang, 2000, J. Med. Chem., 43, 167, 10.1021/jm990333a Kuo, 1993, J. Med. Chem., 36, 1146, 10.1021/jm00061a005 Melikian, A.; Wright, J.J.; Krasinski, A.; Hu, C.; Novack, A.; Kezer, W.B. WO Patent 2007/059108, May, 24, 2007; 2007, Chem. Abstr., 147, 9883 Muller, 2001, Nature, 410, 5, 10.1038/35065016 Geula, 1998, Neurobiology, 51, 518 Ma, 2009, Proc. Natl. Acad. Sci. U.S.A., 106, 15950, 10.1073/pnas.0900903106 Shipe, W.D.; Lindsley, C.; Hallett, D. WO Patent 2007/100366, September 7, 2007; 2007, Chem. Abstr., 147, 343962 Shipe, W.D.; Lindsley, C.; Hallett, D. WO Patent 2007/067489, June 14, 2007; 2007, Chem. Abstr., 147, 72652 Boteva, 2009, Chem. Heterocycl. Compd., 45, 757, 10.1007/s10593-009-0360-1 For some examples concerning the synthesis of Norfloxacin, see: Zhu, 2008, Lett. Org. Chem., 5, 1, 10.2174/157017808783330126 Bambeke, 2005, Clin. Microbiol. Infect., 11, 256, 10.1111/j.1469-0691.2005.01131.x Mitscher, 2005, Chem. Rev., 105, 559, 10.1021/cr030101q Kalkote, 1996, Tetrahedron Lett., 37, 6785, 10.1016/S0040-4039(96)01477-3 Pappalardo, 1988, Farmaco, 43, 489 Chu, 1985, J. Heterocycl. Chem., 22, 1033, 10.1002/jhet.5570220421 Koga, 1980, J. Med. Chem., 23, 1358, 10.1021/jm00186a014 For some recent review concerning different aspects of the Morita–Baylis–Hillman reaction, see: Basavaiah, 2007, Chem. Soc. Rev., 36, 1581, 10.1039/b613741p Singh, 2008, Tetrahedron, 64, 4511, 10.1016/j.tet.2008.02.087 Almeida, 2001, Quim. Nova, 23, 98 For new insights about the mechanism of this reaction, see: Santos, 2004, Angew. Chem., Int. Ed., 43, 4330, 10.1002/anie.200460059 Santos, 2006, J. Phys. Org. Chem., 19, 731, 10.1002/poc.1066 Aggarwal, 2005, Angew. Chem., Int. Ed., 44, 1706, 10.1002/anie.200462462 Robiette, 2007, J. Am. Chem. Soc., 129, 15513, 10.1021/ja0717865 Price, 2005, Org. Lett., 7, 147, 10.1021/ol047739o Price, 2005, J. Org. Chem., 70, 3980, 10.1021/jo050202j Roy, 2007, Org. Lett., 9, 4873, 10.1021/ol702211d Amarante, 2009, J. Org. Chem., 74, 3031, 10.1021/jo802578t Amarante, 2009, Chem.—Eur. J., 15, 12460, 10.1002/chem.200900966 For examples for the use of MBH adducts as substrate for natural products synthesis, see: Coelho, 2006, Tetrahedron, 62, 4563, 10.1016/j.tet.2006.02.045 Perez, 2006, Tetrahedron Lett., 47, 1325, 10.1016/j.tetlet.2005.12.058 Silveira, 2005, Tetrahedron Lett., 46, 6477, 10.1016/j.tetlet.2005.07.099 Reddy, 2005, Org. Lett., 7, 2699, 10.1021/ol0508734 Almeida, 2003, Tetrahedron Lett., 44, 937, 10.1016/S0040-4039(02)02765-X Feltrin, 2003, Synth. Commun., 33, 1141, 10.1081/SCC-120017189 Dunn, 2003, Org. Process Res. Dev., 7, 244, 10.1021/op020091f Rossi, 2002, Tetrahedron Lett., 42, 2797 Mateus, 2001, Tetrahedron, 57, 6901, 10.1016/S0040-4020(01)00647-0 Iwabuchi, 2001, Chem. Commun., 2030, 10.1039/b106471c Mateus, 2005, J. Braz. Chem. Soc., 16, 386, 10.1590/S0103-50532005000300012 McCauley, 1998, J. Am. Chem. Soc., 120, 7647, 10.1021/ja981257o Coelho, 1989, Tetrahedron Lett., 30, 565, 10.1016/S0040-4039(00)95255-9 For recent examples of the use of MBH adducts as starting materials for heterocycles synthesis, see: Vaithiyanathan, 2009, Synlett, 1591 Ravinder, 2009, Tetrahedron Lett., 50, 4229, 10.1016/j.tetlet.2009.04.136 Zhong, 2009, Synthesis, 2333 Narender, 2009, Helv. Chim. Acta, 92, 959, 10.1002/hlca.200800352 Bakthadoss, 2009, Synlett, 1014, 10.1055/s-0028-1088206 Pirovani, 2009, Synlett, 2333 Meng, 2009, Org. Lett., 11, 137, 10.1021/ol802453c Kim, 2009, Tetrahedron Lett., 50, 1249, 10.1016/j.tetlet.2009.01.018 Han, 2009, Tetrahedron, 65, 9616, 10.1016/j.tet.2009.09.047 Lee, 2008, Tetrahedron, 64, 7183, 10.1016/j.tet.2008.05.087 He, 2007, J. Org. Chem., 72, 7466, 10.1021/jo071247i Lee, 2007, Tetrahedron Lett., 48, 4119, 10.1016/j.tetlet.2007.04.022 Park, 2005, Bull. Korean Chem. Soc., 26, 1440, 10.5012/bkcs.2005.26.9.1440 2005, Chem. Abstr., 144, 350460 Lee, 2005, Tetrahedron, 61, 1493, 10.1016/j.tet.2004.11.082 Basavaiah, 2004, J. Org. Chem., 69, 7379, 10.1021/jo0489871 Coelho, 2003, Tetrahedron Lett., 44, 5731, 10.1016/S0040-4039(03)01307-8 O’Dell, 2003, J. Org. Chem., 68, 6427, 10.1021/jo034447c Kim, 2002, Curr. Org. Chem., 6, 627, 10.2174/1385272023374094 Kim, 2002, Tetrahedron Lett., 43, 6209, 10.1016/S0040-4039(02)01314-X Basavaiah, 2002, Tetrahedron, 58, 3693, 10.1016/S0040-4020(02)00332-0 Kim, 2001, Tetrahedron Lett., 42, 3737, 10.1016/S0040-4039(01)00552-4 Hong, 2006, Synthesis, 963 Kim, 2000, Org. Lett., 2, 343, 10.1021/ol9903741 For examples of ESI-MS monitoring of key organic reactions see: Eberlin, 2003, Org. Lett., 5, 1391, 10.1021/ol027439b Sabino, 2004, Angew. Chem., Int. Ed., 43, 2514, 10.1002/anie.200353076 Pla-Quintana, 2005, ARKIVOC, IX, 51, 10.3998/ark.5550190.0006.907 Furmeier, 2005, Chem.—Eur. J., 11, 5545, 10.1002/chem.200500188 Masllorens, 2003, Org. Lett., 5, 1559, 10.1021/ol034340b Jayakannan, 2001, Macromolecules, 34, 5386, 10.1021/ma0100403 Aliprantis, 1994, J. Am. Chem. Soc., 116, 6985, 10.1021/ja00094a083 De Souza, 2009, Chem.—Eur. J., 15, 9799, 10.1002/chem.200900470 2010 Amarante, 2006, Tetrahedron Lett., 47, 8427, 10.1016/j.tetlet.2006.09.037 Coelho, 2002, Tetrahedron, 58, 7437, 10.1016/S0040-4020(02)00822-0 Almeida, 1998, Tetrahedron Lett., 39, 8609, 10.1016/S0040-4039(98)01927-3 Lee, 2003, Tetrahedron, 59, 385, 10.1016/S0040-4020(02)01518-1 Said, 2001, Tetrahedron: Asymmetry, 12, 893, 10.1016/S0957-4166(01)00130-6 Ordoukhanian, 1995, J. Am. Chem. Soc., 117, 9570, 10.1021/ja00142a028 Yoo, 2006, Tetrahedron Lett., 47, 125, 10.1016/j.tetlet.2005.10.143 Rosenthal, 2003, J. Chem. Educ., 80, 679, 10.1021/ed080p679 Blanskepoor, 2007, J. Chem. Educ., 84, 697, 10.1021/ed084p697 Lager, 2006, J. Med. Chem., 49, 2526, 10.1021/jm058057p Mazuel, 1991, Norfloxacin, 557, 10.1016/S0099-5428(08)60540-7