Syntheses of side-chain fluorinated biologically important imidazoles and indoles

Journal of Fluorine Chemistry - Tập 125 - Trang 501-508 - 2004
Bohumil Dolensky1, Ghilsoo Nam1, Wei-Ping Deng1, Jayan Narayanan1, Junfa Fan1, Kenneth L. Kirk1
1Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Department of Health and Human Services, Building 8A, Room B1A-02, 8 Center Drive, MSC 0810, Bethesda, MD 20892, USA

Tài liệu tham khảo

Kirk, 1971, J. Am. Chem. Soc., 93, 3060, 10.1021/ja00730a066 K.L. Kirk, L.A. Cohen, in: R. Filler (Ed.), Biochemistry of the CarbonFluorine Bond, ACS Symposium Series, 1976, pp. 23–36. Torrence, 1979, Biochem. Pharmacol., 28, 1565, 10.1016/0006-2952(79)90475-1 K.L. Kirk, D. Cantacuzene, C.R. Creveling, in: R. Filler, Y. Kobayashi (Eds.), Biomedicinal Aspects of Fluorine Chemistry, Kodansha, Tokyo, 1982, pp. 75–91. Kirk, 1976, J. Heterocyclic Chem., 13, 1253, 10.1002/jhet.5570130622 J. Kollonitsch, in: R. Filler, Y. Kobayashi (Eds.), Biomedicinal Aspects of Fluorine Chemistry, Kodansha, Tokyo, 1982, pp. 93–122 N. Sewald, K. Burger, in: V.P. Kukharand, V. Soloshonok (Eds.), Fluorine Containing Amino Acids, Wiley, New York, 1995, pp. 139–220 Silverman, 1976, Biochemistry, 15, 4718, 10.1021/bi00666a028 R.W. Fuller, B.B. Molloy, in: R. Filler (Ed.), Biochemistry of the CarbonFluorine Bond, ACS Symposium Series, 1976, pp. 77–98. Kimoto, 1978, J. Org. Chem., 43, 3403, 10.1021/jo00411a036 Hayakawa, 1998, J. Org. Chem., 63, 9448, 10.1021/jo9814952 Kimoto, 1992, J. Fluorine Chem., 59, 197, 10.1016/S0022-1139(00)82410-0 Kobayashi, 1974, J. Org. Chem., 39, 18361848, 10.1021/jo00927a010 LeTourneau, 1984, Tetrahedron Lett., 25, 5227, 10.1016/S0040-4039(01)81570-7 Kollonitsch, 1979, J. Org. Chem., 44, 771, 10.1021/jo01319a023 Dolensky, 2003, Collect. Czech. Chem. Commun., 67, 1335, 10.1135/cccc20021335 G. Alvernhe, A. Laurent, G. Haufe, Synthesis (1987) 562–564 Haufe, 1999, Org. Synth., 76, 159, 10.15227/orgsyn.076.0159 Matsubara, 1988, Tetrahedron, 44, 2855, 10.1016/S0040-4020(88)90021-X Suga, 1990, Tetrahedron, 46, 42554260 Oldendorf, 2000, J. Prakt. Chem, 342, 52, 10.1002/(SICI)1521-3897(200001)342:1<52::AID-PRAC52>3.0.CO;2-H Dolensky, 2001, J. Org. Chem., 66, 4687, 10.1021/jo0102415 Rétey, 1994, Arch. Biochem. Biophys., 314, 1, 10.1006/abbi.1994.1405 DeFabo, 1983, J. Exp. Med., 158, 84, 10.1084/jem.158.1.84 Garssen, 1999, Immunology, 96, 298, 10.1046/j.1365-2567.1999.00698.x Percy, 1998, J. Fluorine Chem., 91, 5, 10.1016/S0022-1139(98)00196-1 Boguslavskaya, 1972, Russ. Chem. Rev., 41, 740, 10.1070/RC1972v041n09ABEH002089 Boguslavskaya, 1984, Russ. Chem. Rev., 53, 1178, 10.1070/RC1984v053n12ABEH003147 Yoneda, 1990, Tetrahedron, 47, 5329, 10.1016/S0040-4020(01)80970-4 Cabaleiro, 1987, J. Chem. Soc., Perkin Trans., 2, 1473, 10.1039/p29870001473 Zupan, 1976, J. Chem. Soc., Perkin Trans., 1, 971, 10.1039/p19760000971 Gregorcic, 1984, J. Fluorine Chem., 24, 291, 10.1016/S0022-1139(00)81318-4 Gregorcic, 1984, J. Org. Chem., 49, 333, 10.1021/jo00176a022 Dolensky, 2002, J. Org. Chem., 67, 3468, 10.1021/jo0200419 Dolensky, 2003, J. Fluorine Chem., 124, 105, 10.1016/S0022-1139(03)00197-0 Dolensky, 2003, J. Fluorine Chem., 123, 95, 10.1016/S0022-1139(03)00096-4 Correa, 1996, Tetrahedron Lett., 37, 9259, 10.1016/S0040-4039(96)02138-7 Warrington, 1996, Anticancer Res., 16, 3629 Warrington, 1996, Anticancer Res., 16, 3641 Stolfi, 1990, Chemotherapy, 36, 435, 10.1159/000238801 D.-W. Shen, M. Gottesman, K.L. Kirk, unpublished data. B.E. Smart, in: R.E. Banks, B.E. Smart, J.C. Tatlow (Eds.), Organofluorine Chemistry, Principles and Commercial Applications, Plenum Press, New York, 1994, pp. 57–88. Deng, 2003, J. Org. Chem., 68, 2798, 10.1021/jo020731c Bergman, 1973, Tetrahedron, 29, 971, 10.1016/0040-4020(73)80047-X G.S. Lal, G.P. Pez, R.J. Pesaresi, F.M. Prozonic, Chem. Commun. (1999) 215–216.