17β-HSD2 inhibitors for the treatment of osteoporosis: Identification of a promising scaffold

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 2, 2011, Pages 807-815

  Wetzel, Marie ^a   Marchais Oberwinkler, Sandrine ^a   Hartmann, Rolf W ^a,b  

^a SAARLAND UNIVERSITY   (Germany)

^b SAARLAND UNIVERSITY   (Germany)

Author keywords

17 HSD2; Hydroxymethylphenyl; Hydroxyphenyl; Non steroidal inhibitors; Osteoporosis; Steroidomimetics; Substituted hydroxynaphthyl

Indexed keywords

3 (5 HYDROXY 2 NAPHTHYL)N METHYLBENZAMIDE; 4 (5 HYDROXY 2 NAPHTHYL)N METHYLBENZENESULFONAMIDE; ENZYME INHIBITOR; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; N(4' HYDROXYBIPHENYL 3 YL) 2 (3 HYDROXYPHENYL)N METHYLACETAMIDE; N(4' HYDROXYBIPHENYL 3 YL)N METHYLBENZAMIDE; N[3 (5 HYDROXY 2 NAPHTHYL)PHENYL]ACETAMIDE; N[4 (5 HYDROXY 2 NAPHTHYL)PHENYL]METHANESULFONAMIDE; TESTOSTERONE 17BETA DEHYDROGENASE; TESTOSTERONE 17BETA DEHYDROGENASE 1; TESTOSTERONE 17BETA DEHYDROGENASE 2; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG ACTIVITY; DRUG SELECTIVITY; DRUG SYNTHESIS; IC 50; OSTEOPOROSIS;

17-HYDROXYSTEROID DEHYDROGENASES; BIPHENYL COMPOUNDS; ENZYME INHIBITORS; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; FEMALE; HUMANS; MALE; NAPHTHALENES; OSTEOPOROSIS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 78651480234     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.12.013     Document Type: Article

References (50)

1. J.E. Compston Physiol. Rev. 81 2001 419
2. B. Frenkel, A. Hong, S.K. Baniwal, G.A. Coetzee, C. Ohlsson, O. Khalid, and Y. Gabet J. Cell. Physiol. 224 2010 305
3. U.A. Liberman, S.R. Weiss, J. Broll, H.W. Minne, H. Quan, N.H. Bell, J. Rodriguez-Portales, R.W. Downs Jr., J. Dequeker, M. Favus, E. Seeman, R.R. Recker, T. Capizzi, A.C.I. Santora, A. Lombardi, R.V. Shah, L.J. Hirsch, and D.B. Karpf N. Eng. J. Med. 333 1995 1437
4. D.C. Bauer, D.M. Black, P. Garnero, M. Hochberg, S. Ott, J. Orloff, D.E. Thompson, S.K. Ewing, and P.D. Delmas J. Bone Miner. Res. 19 2004 1250
5. E. Orwoll, M. Ettinger, S. Weiss, P. Miller, D. Kendler, J. Graham, S. Adami, K. Weber, R. Lorenc, P. Pietschmann, K. Vandormael, and A. Lombardi N. Eng. J. Med. 343 2000 604
6. B. Ettinger, D.M. Black, B.H. Mitlak, R.K. Knickerbocker, T. Nickelsen, H.K. Genant, C. Christiansen, P.D. Delmas, J.R. Zanchetta, J. Stakkestad, C.C. Glüer, K. Krueger, F.J. Cohen, S. Eckert, K.E. Ensrud, L.V. Avioli, P. Lips, and S.R. Cummings JAMA 282 1999 637
7. E. Barrett-Connor, L. Mosca, P. Collins, M.J. Geiger, D. Grady, M. Kornitzer, M.A. McNabb, and N.K. Wenger N. Eng. J. Med. 355 2006 125
8. R.T. Turner, B.L. Riggs, and T.C. Spelsberg Endocr. Rev. 15 1994 275
9. X. Chen, Y. Deng, Z. Zhou, Q. Tao, J. Zhu, X. Li, J. Chen, and J. Hou Vet. Res. Commun. 34 2010 143
10. S.K. Mok, W.F. Chen, W.P. Lai, P.C. Leung, X.L. Wang, X.S. Yao, and M.S. Wong Br. J. Pharmacol. 159 2010 939
11. R. Eastell, and A. Blumsohn J. Rheumatol. 24 1997 1215
12. M. Le Borgne, P. Marchand, M. Duflos, B. Delevoye-Seiller, S. Piessard-Robert, G. Le Baut, R.W. Hartmann, and M. Palzer Arch. Pharm. 330 1997 141
13. S. Haidar, P.B. Ehmer, S. Barassin, C. Batzl-Hartmann, and R.W. Hartmann J. Steroid Biochem. Mol. Biol. 84 2003 555
14. F. Leroux, T.U. Hutschenreuter, C. Charrire, R. Scopelliti, and R.W. Hartmann Helv. Chim. Acta 86 2003 2671
15. M. Frotscher, E. Ziegler, S. Marchais-Oberwinkler, P. Kruchten, A. Neugebauer, L. Fetzer, C. Scherer, U. Müller-Vieira, J. Messinger, H. Thole, and R.W. Hartmann J. Med. Chem. 51 2008 2158
16. S. Marchais-Oberwinkler, P. Kruchten, M. Frotscher, E. Ziegler, A. Neugebauer, U. Bhoga, E. Bey, U. Müller-Vieira, J. Messinger, H. Thole, and R.W. Hartmann J. Med. Chem. 51 2008 4685
17. E. Bey, S. Marchais-Oberwinkler, R. Werth, M. Negri, Y.A. Al-Soud, P. Kruchten, A. Oster, M. Frotscher, B. Birk, and R.W. Hartmann J. Med. Chem. 51 2008 6725
18. E. Bey, S. Marchais-Oberwinkler, M. Negri, P. Kruchten, A. Oster, T. Klein, A. Spadaro, R. Werth, M. Frotscher, B. Birk, and R.W. Hartmann J. Med. Chem. 52 2009 6724
19. A. Oster, T. Klein, R. Werth, P. Kruchten, E. Bey, M. Negri, S. Marchais-Oberwinkler, M. Frotscher, and R.W. Hartmann Bioorg. Med. Chem. 18 2010 3494
20. E. Baston, and R.W. Hartmann Bioorg. Med. Chem. Lett. 9 1999 1601
21. F. Picard, E. Baston, W. Reichert, and R.W. Hartmann Bioorg. Med. Chem. 8 2000 1479
22. F. Picard, T. Schulz, and R.W. Hartmann Bioorg. Med. Chem. 10 2002 437
23. M.L. Lu, Y.W. Huang, and S.X. Lin J. Biol. Chem. 277 2002 22123
24. Y. Dong, Q.Q. Qiu, J. Debear, W.F. Lathrop, D.R. Bertolini, and P.P. Tamburini J. Bone Miner. Res. 13 1998 1539
25. B.C. van der Eerden, C.W. Lowik, J.M. Wit, and M. Karperien J. Endocrinol. 180 2004 457
26. K. Sam, F. Labrie, and D. Poirier Eur. J. Med. Chem. 35 2000 217
27. D. Poirier, P. Bydal, M.R. Tremblay, K.M. Sam, and V. Luu-The Mol. Cell. Endocrinol. 171 2001 119
28. P. Bydal, S. Auger, and D. Poirier Steroids 69 2004 325
29. J. Wood, C.M. Bagi, C. Akuche, A. Bacchiocchi, J. Baryza, M.L. Blue, C. Brennan, A.M. Campbell, S. Choi, J.H. Cook, P. Conrad, B.R. Dixon, P.P. Ehrlich, T. Gane, D. Gunn, T. Joe, J.S. Johnson, J. Jordan, R. Kramss, P. Liu, J. Levy, D.B. Lowe, I. McAlexander, R. Natero, A.M. Redman, W.J. Scott, C. Town, M. Wang, Y. Wang, and Z. Zhang Bioorg. Med. Chem. Lett. 16 2006 4965
30. K. Kristan, K. Krajnc, J. Konc, S. Gobec, J. Stojan, and T. Lanišnik Rižner Steroids 70 2005 626
31. C.M. Bagi, J. Wood, D. Wilkie, and B. Dixon J. Musculoskelet. Neuronal Interact. 8 2008 267
32. L. Wu, M. Einstein, W.M. Geissler, H.K. Chan, K.O. Elliston, and S. Andersson J. Biol. Chem. 268 1993 12964
33. L.W.L. Woo, N.M. Howarth, A. Purohit, H.A.M. Hejaz, M.J. Reed, and B.V.L. Potter J. Med. Chem. 41 1998 1068
34. R.E. Mewshaw, R.J. Edsall Jr., C. Yang, E.S. Manas, Z.B. Xu, R.A. Henderson, J.C. Keith Jr., and H.A. Harris J. Med. Chem. 48 2005 3953
35. T.R. Kasturi, and T. Arunachalam Can. J. Chem. 46 1968 3625
36. J. Koubachi, S. El Kazzouli, S. Berteina-Raboin, A. Mouaddib, and G. Guillaumet J. Org. Chem. 72 2007 7650
37. M.T. Herrero, I. Tellitu, E. Domínguez, S. Hernández, I. Moreno, and R. SanMartín Tetrahedron 58 2002 8581
38. M.V. Bhatt, and S.U. Kulkarni Synthesis 1983 1983 249
39. S.X. Lin, F. Yang, J.Z. Jin, R. Breton, D.W. Zhu, V. Luu-The, and F. Labrie J. Biol. Chem. 267 1992 16182
40. D.W. Zhu, X. Lee, R. Breton, D. Ghosh, W. Pangborn, W.L. Duax, and S.X. Lin J. Mol. Biol. 234 1993 242
41. P. Kruchten, R. Werth, S. Marchais-Oberwinkler, M. Frotscher, and R.W. Hartmann Mol. Cell. Endocrinol. 301 2009 154
42. L.J. Dominguez, R. Scalisi, and M. Barbagallo Acta Biomed. 81 2010 55
43. F. Minutolo, M. Macchia, B.S. Katzenellenbogen, and J.A. Katzenellenbogen Med. Res. Rev. 2009
44. B.T. Zhu, G.Z. Han, J.Y. Shim, Y. Wen, and X.R. Jiang Endocrinology 147 2006 4132
45. M. Mazumdar, D. Fournier, D.W. Zhu, C. Cadot, D. Poirier, and S.X. Lin Biochem. J. 424 2009 357 and references therein
46. W. Chen, Z. Lin, M. Ning, C. Yang, X. Yan, Y. Xie, X. Shen, and M.W. Wang Bioorg. Med. Chem. 15 2007 5828
47. Cusack, K. S.-G., J. A.; Gordon, T. D.; Barberis, C. E.; Allen, H. J.; Bischoff, A. K.; Ericsson, A. M.; Friedman, M. M.; George, D. M.; Roth, G. P.; Talanian, R. V.; Thomas, C.; Wallace, G. A.; Wishart, N.; Yu, Z. 2007, WO 2005110410 (A2).
48. W. Qiu, R.L. Campbell, A. Gangloff, P. Dupuis, R.P. Boivin, M.R. Tremblay, D. Poirier, and S.X. Lin FASEB J. 16 2002 1829
49. J. Zimmermann, R. Liebl, and E. von Angerer J. Steroid Biochem. Mol. Biol. 94 2005 57
50. R.W. Hartmann J. Med. Chem. 29 1986 1668