Carboxylic acid and phosphate ester derivatives of fluconazole: synthesis and antifungal activities

Bioorganic & Medicinal Chemistry - Tập 12 - Trang 6255-6269 - 2004
Nguyen-Hai Nam1, Soroush Sardari1, Meredith Selecky1, Keykavous Parang1
1Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, 41 Lower College Road, Kingston, RI 02881, USA

Tài liệu tham khảo

Fridkin, 1996, Clin. Microbiol. Rev., 9, 499, 10.1128/CMR.9.4.499 Larocco, 1997, Clin. Microbiol. Rev., 10, 277, 10.1128/CMR.10.2.277 Patel, 1997, Clin. Microbiol. Rev., 10, 86, 10.1128/CMR.10.1.86 Tuite, 1996, Trends Biotechnol., 14, 219, 10.1016/0167-7799(96)30011-5 Walsh, 1995, Clin. Infect. Dis., 20, 900, 10.1093/clinids/20.4.900 Lacaz, 2002, Rev. Inst. Med. Trop. Sao Paulo, 44, 225, 10.1590/S0036-46652002000400008 Perfect, 1992, Drug Safety, 7, 323, 10.2165/00002018-199207050-00003 Sabra, 1990, Drug Safety, 5, 94, 10.2165/00002018-199005020-00003 Kauffman, 1997, Drugs, 53, 539, 10.2165/00003495-199753040-00001 Schmitt, 1992, Chemotherapy, 38, 118, 10.1159/000238951 Zakula, 1997, J. Antimicrob. Chemotherapy, 39, 261, 10.1093/jac/39.2.261 Tsukuda, 1998, Bioorg. Med. Chem. Lett., 8, 1819, 10.1016/S0960-894X(98)00316-3 Rex, 1995, Antimicrob. Agents Chemother., 39, 1, 10.1128/AAC.39.1.1 Wong-Beringer, 2003, Pharmacotherapy, 23, 1441, 10.1592/phco.23.14.1441.31938 Pacetti, 2003, Ann. Pharmacother., 37, 90, 10.1345/aph.1C114 Denning, 2003, Lancet, 362, 1142, 10.1016/S0140-6736(03)14472-8 Wiederhold, 2003, Expert Opin. Invest. Drug., 12, 1313, 10.1517/13543784.12.8.1313 Georgopapadakou, 1996, Antimicrob. Agents Chemother., 40, 279, 10.1128/AAC.40.2.279 Ghannoum, 1997, Dermatol. Ther., 3, 104 Mandala, 1997, J. Biol. Chem., 272, 32709, 10.1074/jbc.272.51.32709 Parang, 1996, Arch. Pharm.-Pharm. Med. Chem., 329, 475, 10.1002/ardp.19963291102 VanMiddlesworth, 1992, J. Antibiot. (Tokyo), 45, 861, 10.7164/antibiotics.45.861 Wang, 1991, J. Biol. Chem., 266, 14486, 10.1016/S0021-9258(18)98712-0 Zweerink, 1992, J. Biol. Chem., 267, 25032, 10.1016/S0021-9258(19)74001-0 Pederson, 1970, Physiol. Plant (Copenh.), 23, 654, 10.1111/j.1399-3054.1970.tb06458.x Nagiec, 1997, J. Biol. Chem., 272, 9809, 10.1074/jbc.272.15.9809 Langner, 1992, J. Biol. Chem., 267, 17159, 10.1016/S0021-9258(18)41908-4 Garg, 1993, Mycose, 36, 51, 10.1111/j.1439-0507.1993.tb00687.x Lodge, 1994, Proc. Natl. Acad. Sci. U.S.A., 91, 12008, 10.1073/pnas.91.25.12008 Weinberg, 1995, Mol. Microbiol., 16, 241, 10.1111/j.1365-2958.1995.tb02296.x Schwartz, 1994, Tetrahedron, 50, 1675, 10.1016/S0040-4020(01)80843-7 Mandala, 1994, J. Antibiot. (Copenh.), 47, 376, 10.7164/antibiotics.47.376 Darwish, 1993, J. Org. Chem., 58, 6072, 10.1021/jo00074a038 Okada, 1989, J. Antibiot. (Tokyo), 42, 276, 10.7164/antibiotics.42.276 Yamamoto, 1991, Chem. Pharma. Bull., 39, 1436, 10.1248/cpb.39.1436 Kubo, 2003, Bioorg. Med. Chem., 11, 1117, 10.1016/S0968-0896(02)00453-4 Ben-Josef, 1997, J. Antibiot. (Tokyo), 50, 937, 10.7164/antibiotics.50.937 Ben-Josef, 2000, Int. J. Antimicrob. Agents, 13, 287, 10.1016/S0924-8579(99)00140-5 Janiak, 2003, Bioorg. Med. Chem., 11, 1653, 10.1016/S0968-0896(03)00049-X Dawson, 1992, J. Antibiot. (Tokyo), 45, 639, 10.7164/antibiotics.45.639 Ponpipom, 1994, J. Med. Chem., 37, 4031, 10.1021/jm00049a022 Aoki, 1993, J. Antibiot. (Tokyo), 46, 952, 10.7164/antibiotics.46.952 VanMiddlesworth, 1996, J. Antibiot. (Tokyo), 49, 329, 10.7164/antibiotics.49.329 Brown, 2003, Immunity, 19, 311, 10.1016/S1074-7613(03)00233-4 Dalle, 2003, Infect. Immun., 71, 7061, 10.1128/IAI.71.12.7061-7068.2003 Wei, 2004, Fungal Genet. Biol., 41, 148, 10.1016/j.fgb.2003.10.006 Parang, 1998, Antiviral Chem. Chemother., 9, 311, 10.1177/095632029800900403 Meylan, 1995, J. Pharm. Sci., 84, 83, 10.1002/jps.2600840120 Galgiani, 1993, Antimicrob. Agents Chemother., 37, 2517, 10.1128/AAC.37.12.2517 National Committee for Clinical Laboratory Standards. Reference method for broth dilution antifungal susceptibility testing for yeasts. Approval standard. Document M27-A. National Committee for Clinical Laboratory Standards, Wayne, PA, 1997; Vol. 17(9) Carballeira, 2004, Arch. Pharm.-Pharm. Med. Chem., 337, 152, 10.1002/ardp.200300824 Hansch, 1995 Sangster, J. LOGKOW Databank. A Databank of Evaluated Octanol–Water Partition Coefficients (LogP) on Microcomputer Diskette, Sangster Research Laboratories, Montreal, Quebec, Canada, 1993 Burkhard, 1985, Chemosphere, 4, 1551, 10.1016/0045-6535(85)90010-4