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Journal of Enzyme Inhibition and Medicinal Chemistry Volume 17, 2002 - Issue 5
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Research Article

6-Substituted 3,4-Dihydro-naphthalene-2-carboxylic Acids: Synthesis and Structure-Activity Studies in a Novel Class of Human 5α Reductase Inhibitors

Eckhard Baston 8.5 Pharmaceutical and Medicinal Chemistry, Saarland University, P.O. Box 15 11 50, D-66041 Saarbrücken, Germany
,
Ola I.A. Salem 8.5 Pharmaceutical and Medicinal Chemistry, Saarland University, P.O. Box 15 11 50, D-66041 Saarbrücken, Germany
&
Rolf W. Hartmann 8.5 Pharmaceutical and Medicinal Chemistry, Saarland University, P.O. Box 15 11 50, D-66041 Saarbrücken, Germany
Pages 303-320 | Published online: 30 Sep 2008

  • McConnell, J.D. and Stoner, E. (2001) Adv. Protein Chem. 56, 143-180.
  • Bartsch, G., Rittmaster, R.S. and Klocker, H. (2002) World J. Urol. 19, 413-425.
  • Prager, N., Bickett, K., French, N. and Marcovici, G. (2002) J. Altern. Complement. Med. 8, 143-152.
  • Cilotti, A., Danza, G. and Serio, M. (2001) J. Endocrinol. Investig. 24, 199-203.
  • Andersson, S., Berman, D.M., Jenkins, E.P. and Russell, D.W. (1991) Nature 354, 159-161.
  • Harris, G., Azzolina, B., Baginsky, W., Cimis, G., Rasmusson, G.H., Tolman, R.L., Raetz, C.R. and Ellsworth, K. (1992) Proc. Natl Acad. Sci. USA 89, 10787-10791.
  • Russell, D.W. and Wilson, J.D. (1994) Annu. Rev. Biochem. 63, 25-61.
  • Ellsworth, K., Azzolina, B., Baginsky, W., Bull, H., Chang, B., Cimis, G., Mitra, S., Toney, J., Bakshi, R.K., Rasmusson, G.R., Tolman, R.L. and Harris, G.S. (1996) J. Steroid Biochem. Mol. Biol. 58, 377-384.
  • Schwartz, J.I., Van Hecken, A., De Schepper, P.J., DeLepeleire, I., Lasseter, K.C., Shamblen, E.G., Winchell, G.A., Constanzen M.L., Chavez, C.M., Wang, D.Z., Ebel, D.L., Justice, S.J. and Gertz, B.J. (1996) J. Clin. Endocrinol. Metab. 81, 2942-3947.
  • Bakshi, R.K., Rasmusson, G.H., Patel, G.F., Mosley, R.T., Chang, B., Ellsworth, K., Harris, G.S. and Tolman, R.L. (1995) J. Med. Chem. 38, 3189-3192.
  • Kojo, H., Nakayama, O., Hirosumi, J., Chida, N., Notsu, Y. and Okuhara, M. (1995) Mol. Pharmacol. 48, 401-406.
  • Bramson, H.N., Hermann, D., Batchelor, K.W., Lee, F.W., James, M.K. and Frye, S.V. (1997) J. Pharmacol. Exp. Ther. 282, 1496-1502.
  • Frye, S.V., Bramson, H.N., Hermann, D.J., Lee, F.W., Sinhababu, A.K. and Tian, G. (1998) Pharm. Biotechnol. 11, 393-422.
  • Sharp, M.J. and Fang, F.G. (1998) Bioorg. Med. Chem. Lett. 8, 3291-3294.
  • McNulty, A.M., Audia, J.E., Bemis, K.G., Goode, R.L., Rocco, V.P. and Neubauer, B.L. (2000) J. Steroid Biochem. Mol. Biol. 72, 13-21.
  • Gisleskog, P.O., Hermann, D., Hammarlund-Udenaes, M. and Karlsson, M.O. (1999) Br. J. Clin. Pharmacol. 47, 53-58.
  • Bartsch, G., Rittmaster, R.S. and Klocker, H. (2000) Eur. Urol. 37, 367-380.
  • Stuart, J.D., Lee, F.W., Simpson Noel, D., Kadwell, S.H., Overton, L.K., Hoffman, C.R., Kost, T.A., Tippin, T.K., Yeager, R.L., Batchelor, K.W. and Bramson, H.N. (2001) Biochem. Pharmacol. 62, 933-942.
  • Wise, G.J. and Md, E.O. (2001) Curr. Urol. Rep. 2, 285-291.
  • Picard, F., Barassin, S., Mokhtarian, A. and Hartmann, R.W. (2002) J. Med. Chem. 45, 3406-3417.
  • Picard, F. and Hartmann, R.W. (2002) J. Enzyme Inhib. Med. Chem. 17, 187-196.
  • Salem, O.I.A., Schulz, T. and Hartmann, R.W. (2002) Arch. Pharm. Pharm. Med. Chem. 335, 83-88.
  • Picard, F., Baston, E., Reichert, W. and Hartmann, R.W. (2000) Bioorg. Med. Chem. 8, 1479-1487.
  • Hartmann, R.W., Hector, M., Haider, S., Ehmer, P.B., Reichert, W. and Jose, J. (2000) J. Med. Chem. 43, 4266-4277.
  • Hartmann, R.W. and Reichert, M. (2000) Arch. Pharm. Pharm. Med. Chem. 333, 145-153.
  • Baston, E. and Hartmann, R.W. (1999) Bioorg. Med. Chem. Lett. 9, 1601-1606.
  • Kattner, L., Göhring, S. and Hartmann, R.W. (1995) Arch. Pharm. Pharm. Med. Chem. 328, 239-245.
  • Hartmann, R.W., Reichert, M. and Göhring, S. (1994) Eur. J. Med. Chem. 29, 807-817.
  • Baston, E., Palusczak, A. and Hartmann, R.W. (2000) Eur. J. Med. Chem. 35, 931-940.
  • Picard, F., Schulz, T. and Hartmann, R.W. (2002) Bioorg. Med. Chem. 10, 437-448.
  • Cereghetti, M., Marbet, R. and Schleich, K. (1982) Helv. Chim. Acta 65, 1318-1330.
  • Baston, E. and Hartmann, R.W. (1998) Synth. Commun. 28, 2725-2729.
  • Liang, T., Cascieri, M.A., Cheung, A.H., Reynolds, G.F. and Rasmusson, G.H. (1985) Endocrinology 117, 571-579.
  • Lowry, O.H., Rosebrough, N.J., Farr, A.L. and Randall, R.J. (1951) J. Biol. Chem. 193, 265-275.
  • Reichert, W., Jose, J. and Hartmann, R.W. (2000) Arch. Pharm. Pharm. Med. Chem. 333, 201-204.
  • Delos, S., Iehle, C., Martin, P.M. and Raynaud, J.P. (1994) J. Steroid Biochem. Mol. Biol. 48, 347-352.
  • Kaefer, M., Audia, J.E., Bruchovsky, N., Goode, R.L., Hsiao, K.C., Leibovitch, I.Y., Krushinski, J.H., Lee, C., Steidle, C.P., Sutkowski, D.M. and Neubauer, B.L. (1996) J. Steroid Biochem. Mol. Biol. 58, 195-205.
  • Cook, S.J., Rawlings, N.C. and Kennedy, R.I. (1982) Steroids 40, 369-380.
  • Segel, I.H. (1993) Enzyme Kinetics: Behavior and Analysis of Rapid Equilibrium and Steady-State Enzyme Systems (John Wiley and Sons Inc., New York).
  • Hu+00E4usler, A., Allegrini, P.R., Biollaz, M., Batzl, Ch., Scheidegger, E. and Bhatnagar, A.S. (1996) J. Steroid Biochem. Mol. Biol. 57, 187-195.
  • Neubert, M.E. and Fishel, D.L. (1979) Mol. Cryst. Liq. Cryst. 53, 101-110.
  • Stang, P.J. and Treptow, W. (1980) Synthesis, 283-284.
  • Stang, P.J. and Fisk, E.T. (1979) Synthesis, 438-440.
  • Cacchi, S. and Lupi, A. (1992) Tetrahedron Lett. 33, 3939-3942.
  • Cacchi, S., Ciattini, P.S., Morera, E. and Ortar, G. (1986) Tetrahedron Lett. 27, 3931-3934.
  • Cacchi, S., Morera, E. and Ortar, G. (1985) Tetrahedron Lett. 26, 1109-1112.
  • Immer, H. and Bagli, J.F. (1968) J. Org. Chem. 33, 2457-2462.
  • Holt, D.A., Levy, M.A. and Metcalf, B.W. (1993) In: Marynoff, B.E. and Marynoff, C.A., eds, Advances in Medicinal Chemistry (JAI Press, Inc., Greenwich, CT) Vol. 2, pp 1-29.
  • Guarna, A., Belle, C., Machetti, F., Occhiato, E.G., Payne, A.H., Cassiani, C., Comerci, A., Danza, G., De Bellis, A., Dini, S., Marrucci, A. and Serio, M. (1997) J. Med. Chem. 40, 1112-1129.
  • Thigpen, A.E., Silver, R.I., Guileyardo, J.M., Casey, M.L., McConnel, J.D. and Russell, D.W. (1993) J. Clin. Investig. 92, 903-910.
  • Normington, K. and Russell, D.W. (1992) J. Biol. Chem. 267, 19548-19554.
  • Berman, D.M. and Russell, D.W. (1993) Proc. Natl Acad. Sci. USA 90, 9359-9363.
  • Hartmann, R.W., Frotscher, M., Ledergerber, D., Wächter, G.A., Grün, G.L. and Sergejew, T.F. (1996) Arch. Pharm. Pharm. Med. Chem. 329, 251-261.
  • Hartmann, R.W., Bayer, H., Grün, G., Sergejew, T., Bartz, U. and Mitrenga, M. (1995) J. Med. Chem. 38, 2103-2111.
  • Hartmann, R.W., Bayer, H. and Grün, G. (1994) J. Med. Chem. 37, 1275-1281.
  • Bayer, H., Batzl, C., Hartmann, R.W. and Mannschreck, A. (1991) J. Med. Chem. 34, 2685-2691.
  • Ranjan, M., Diffley, P., Stephen, G., Price, D., Walton, T.J. and Newton, R.P. (2002) Life Sci. 71, 115-126.
  • Levy, M.A., Brandt, M., Sheedy, K.M., Dinh, J.T., Holt, D.A., Garrison, L.M., Bergsma, D.J. and Metcalf, B.W. (1994) J. Steroid Biochem. Mol. Biol. 48, 197-206.

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