17,20-Lyase inhibitors. Part 3: Design, synthesis, and structure-activity relationships of biphenylylmethylimidazole derivatives as novel 17,20-lyase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 7, 2011, Pages 2428-2442

  Kaku, Tomohiro ^a   Tsujimoto, Saori ^a   Matsunaga, Nobuyuki ^a   Tanaka, Toshimasa ^a   Hara, Takahito ^a   Yamaoka, Masuo ^a   Kusaka, Masami ^a   Tasaka, Akihiro ^a  

^a TAKEDA PHARMACEUTICAL COMPANY LIMITED   (Japan)

Author keywords

17,20 Lyase; DHEA; Prostate cancer; Testosterone

Indexed keywords

1 (1,1' BIPHENYL) 3 YL 1 (1H IMIDAZOL 4 YL) 2 METHYL 1 PROPANOL; 1 (1,1' BIPHENYL) 4 YL 1 (1H IMIDAZOL 4 YL) 2 METHYL 1 PROPANOL; 1 (1H IMIDAZOL 4 YL) 1 [4' METHOXY (1,1' BIPHENYL) 3 YL] 2 METHYL 1 PROPANOL; 1 (1H IMIDAZOL 4 YL) 1 [4' METHOXY (1,1' BIPHENYL) 4 YL] 2 METHYL 1 PROPANOL; 1 (3 BROMOPHENYL) 2 METHYL 1 (1 TRITYL 1H IMIDAZOL 4 YL) 1 PROPANOL; 1 (4 BROMOPHENYL) 2 METHYL 1 (1 TRITYL 1H IMIDAZOL 4 YL) 1 PROPANOL; 1 [4' CHLORO(1,1' BIPHENYL) 3 YL] 1 (1H IMIDAZOL 4 YL) 2 METHYL 1 PROPANOL; 1 [4' CHLORO(1,1' BIPHENYL) 3 YL] 2 METHYL 1 (1 TRITYL 1H IMIDAZOL 4 YL) 1 PROPANOL; 1 [4' CHLORO(1,1' BIPHENYL) 4 YL] 1 (1 TRITYL 1H IMIDAZOL 4 YL) 2 METHYL 1 PROPANOL; 1 [4' CHLORO(1,1' BIPHENYL) 4 YL] 1 (1H IMIDAZOL 4 YL) 2 METHYL 1 PROPANOL; 1 [4' FLUORO(1,1' BIPHENYL) 3 YL] 1 (1H IMIDAZOL 4 YL) 2 METHYL 1 PROPANOL; 1 [4' FLUORO(1,1' BIPHENYL) 3 YL] 2 METHYL 1 (1 TRITYL 1H IMIDAZOL 4 YL) 1 PROPANOL; 1 [4' FLUORO(1,1' BIPHENYL) 4 YL] 1 (1 TRITYL 1H IMIDAZOL 4 YL) 2 METHYL 1 PROPANOL; 1 [4' FLUORO(1,1' BIPHENYL) 4 YL] 1 (1H IMIDAZOL 4 YL) 2 METHYL 1 PROPANOL; 17,20 LYASE INHIBITOR; ACETAMIDE DERIVATIVE; BIPHENYL DERIVATIVE; BIPHENYLYLMETHYLIMIDAZOLE DERIVATIVE; CYTOCHROME P450; CYTOCHROME P450 2C5; CYTOCHROME P450 3A4; ENZYME INHIBITOR; N [4' [1 HYDROXY 1 (1H IMIDAZOL 4 YL) 2 METHYLPROPYL](1,1' BIPHENYL) 3 YL]ACETAMIDE; N [4' [1 HYDROXY 1 (1H IMIDAZOL 4 YL) 2 METHYLPROPYL](1,1' BIPHENYL) 4 YL]ACETAMIDE; N [4' [1 HYDROXY 2 METHYL 1 (1 TRITYL 1H IMIDAZOL 4 YL)PROPYL](1,1' BIPHENYL) 4 YL]ACETAMIDE; PRASTERONE; STEROID 17,20 LYASE; TESTOSTERONE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL EXPERIMENT; ARTICLE; DRUG DESIGN; DRUG MECHANISM; DRUG SYNTHESIS; ENANTIOMER; ENZYME INHIBITION; IC 50; NONHUMAN; SINGLE DRUG DOSE; STRUCTURE ACTIVITY RELATION; TESTOSTERONE BLOOD LEVEL;

ANIMALS; CRYSTALLOGRAPHY, X-RAY; CYTOCHROME P-450 CYP3A; ENZYME INHIBITORS; HUMANS; IMIDAZOLES; INHIBITORY CONCENTRATION 50; MACACA FASCICULARIS; MALE; MODELS, MOLECULAR; RATS; RATS, SPRAGUE-DAWLEY; STEROID 17-ALPHA-HYDROXYLASE; STRUCTURE-ACTIVITY RELATIONSHIP;

MAMMALIA; RATTUS;

EID: 79953181225     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.02.009     Document Type: Article

References (51)

1. B.A. Hellerstedt, and K.J. Pienta CA Cancer J. Clin. 52 2002 154
2. National Comprehensive Cancer Network. NCCN Clinical Practice Guidelines in Oncology: Prostate Cancer v1.2010. 2010.
3. F. Labrie, A. Dupont, A. Belanger, L. Cusan, Y. Lacourciere, G. Monfette, J.G. Laberge, J.P. Emond, A.T. Fazekas, J.P. Raynaud, and J.M. Husson Clin. Invest. Med. 5 1982 267
4. Prostate Cancer Trialists' Collaborative Group Lancet 355 2000 1491
5. W.G. Nelson, A.M. De Marzo, and W.B. Isaacs N. Eng. J. Med. 349 2003 366
6. W.L. Miller Endocr. Rev. 9 1988 295
7. R. De Coster, W. Wouters, and J. Bruynseels J. Steroid Biochem. Mol. Biol. 56 1996 133
8. J.A. Locke, L. Fazli, H. Adomat, J. Smyl, K. Weins, A.A. Lubik, D.B. Hales, C.C. Nelson, M.E. Gleave, and E.S. Tomlinson Guns Prostate 69 2009 928
9. H. Van den Bossche J. Steroid Biochem. Mol. Biol. 43 1992 1003
10. G.A. Potter, S.E. Barrie, M. Jarman, and M.G. Rowlands J. Med. Chem. 38 1995 2463
11. J. Li, Y. Li, C. Son, and A. Brodie J. Med. Chem. 39 1996 4335
12. V.C.O. Njar, M. Hector, and R.W. Hartmann Bioorg. Med. Chem. 4 1996 1447
13. Y. Ling, J. Li, Y. Liu, K. Kato, G.T. Klus, and A.M.H. Brodie J. Med. Chem. 40 1997 3297
14. Y. Ling, J. Li, K. Kato, Y. Liu, X. Wang, G.T. Klus, K. Marat, I.P. Nnane, and A.M.H. Brodie Bioorg. Med. Chem. 6 1998 1683
15. V.C.O. Njar, K. Kato, I.P. Nnane, D.N. Grigoryev, B.J. Long, and A.M.H. Brodie J. Med. Chem. 41 1998 902
16. M. Jarman, J.H. Smith, P.J. Nicholls, and C. Simons Nat. Prod. Rep. 24 1998 495
17. V.C.O. Njar, and A.M.H. Brodie Curr. Pharm. Des. 5 1999 163
18. R. McCague, M.G. Rowlands, S.E. Barrie, and J. Houghton J. Med. Chem. 33 1990 3050
19. T. Sergejew, and R.W. Hartmann J. Enzyme Inhib. 8 1994 113
20. S. Ahmed, J.H. Smith, P.J. Nicholls, R. Whomsley, and P. Cariuk Drug Des. Discuss. 13 1995 27
21. M.G. Rowlands, S.E. Barrie, F. Chan, M. Jarman, R. McCague, and G.A. Potter J. Med. Chem. 38 1995 4191
22. R.W. Hartmann, G.A. Wächter, T. Sergejew, R. Würtz, and J. Düerkop Arch. Pharm. Pharm. Med. Chem. 328 1995 573
23. G.A. Wächter, R.W. Hartmann, T. Sergejew, G.L. Grün, and D. Ledergerber J. Med. Chem. 39 1996 834
24. R.W. Hartmann, M. Frotscher, D. Ledergerber, G.A. Wächter, G.L. Grün, and T.F. Sergejew Arch. Pharm. Pharm. Med. Chem. 329 1996 251
25. A.M. Al-Hamrouni, M. Ahmadi, P.J. Nicholls, J.H. Smith, P. Lombardi, and V. Pestellini Pharm. Sci. 3 1997 259
26. Y. Ideyama, M. Kudoh, K. Tanimoto, Y. Susaki, T. Nanya, T. Nakahara, H. Ishikawa, T. Yoden, M. Okada, T. Fujikura, H. Akaza, and H. Shikama Prostate 37 1998 10
27. Y. Zhuang, and R.W. Hartmann Arch. Pharm. Pharm. Med. Chem. 331 1998 36
28. Y. Zhuang, and R.W. Hartmann Arch. Pharm. Pharm. Med. Chem. 332 1999 25
29. B.W. Wachall, M. Hector, Y. Zhuang, and R.W. Hartmann Bioorg. Med. Chem. 7 1999 1913
30. Y. Zhuang, B.W. Wachall, and R.W. Hartmann Bioorg. Med. Chem. 8 2000 245
31. R.W. Hartmann, M. Hector, S. Haidar, P. Ehmer, W. Reichert, and J. Jose Med. Chem. 43 2000 4266
32. R.W. Hartmann, M. Hector, B.G. Wachall, A. Paluszcak, M. Palzer, V. Huch, and M. Veith J. Med. Chem. 43 2000 4437
33. S. Haidar, and R.W. Hartmann Arch. Pharm. 335 2002 526
34. R.W. Hartmann, P.B. Ehmer, S. Haidar, M. Hector, J. Jose, C.D.P. Klein, S.B. Seidel, T. Sergejew, B.G. Wachall, G.A. Wächter, and Y. Zhuang Arch. Pharm. 335 2002 119
35. S. Haidar, P.B. Ehmer, S. Barassin, C. Batzl-Hartmann, and R.W. Hartmann J. Steroid Biochem. Mol. Biol. 84 2003 555
36. O.O. Clement, C.M. Freeman, R.W. Hartmann, A. Paluszcak, V.D. Handratta, T.S. Vasaitis, A.M.H. Brodie, and V.C.O. Njar J. Med. Chem. 46 2003 2345
37. M.A.E. Pinto-Bazurco Mendieta, M. Negri, C. Jagusch, U.E. Hille, U. Müller-Vieira, D. Schmidt, K. Hansen, and R.W. Hartmann Bioorg. Med. Chem. Lett. 18 2008 267
38. M.A.E. Pinto-Bazurco Mendieta, M. Negri, C. Jagusch, U. Müller-Vieira, T. Lauterbach, and R.W. Hartmann J. Med. Chem. 51 2008 5009
39. Y. Zhuang, B.G. Wachall, and R.W. Hartmann Bioorg. Med. Chem. 8 2000 1245
40. F. Leroux, T. Hutschenreuter, C. Charrire, R. Scopelliti, and R.W. Hartmann Helv. Chim. Acta 86 2003 2671
41. T.U. Hutschenreuter, P.B. Ehmer, and R.W. Hartmann J. Enzyme Inhib. Med. Chem. 18 2004 17
42. C. Jagusch, M. Negri, U.E. Hille, Q. Hu, M. Bartels, K. Jahn-Hoffmann, M.A.E. Pinto-Bazurco Mendieta, B. Rodenwaldt, U. Müller-Vieira, D. Schmidt, T. Lauterbach, M. Recanatini, A. Cavalli, and R.W. Hartmann Bioorg. Med. Chem. 16 2008 1992
43. Q. Hu, M. Negri, K. Jahn-Hoffmann, Y. Zhuang, S. Olgen, M. Bartels, U. Müller-Vieira, T. Lauterbach, and R.W. Hartmann Bioorg. Med. Chem. 16 2008 7715
44. N. Matsunaga, T. Kaku, F. Itoh, T. Tanaka, T. Hara, H. Miki, M. Iwasaki, T. Aono, M. Yamaoka, M. Kusaka, and A. Tasaka Bioorg. Med. Chem. 12 2004 2251
45. Tasaka, A.; Kaku, T.; Kusaka, M. 1-Substituted phenyl-1-(1H-imidazol-4- yl) alcohols, process for producing the same and use thereof. WO/2001/030764.
46. N. Matsunaga, T. Kaku, A. Ojida, T. Tanaka, T. Hara, H. Miki, M. Iwasaki, M. Yamaoka, M. Kusaka, and A. Tasaka Bioorg. Med. Chem. 12 2004 4313
47. J.-I. Kawakami, K. Kimura, and M. Yamaoka Synthesis 5 2003 677
48. T. Fujita, H. Tsuji, H. Deura, and M. Nakajima Agric. Biol. Chem. 33 1969 785
49. J. Ohkanda, J.W. Lockman, M.A. Kothare, Y. Qian, M.A. Blaskovich, S.M. Sebti, and A.D. Hamilton J. Med. Chem. 45 2002 177
50. A. Tasaka, N. Tamura, Y. Matsushita, K. Teranishi, R. Hayashi, K. Okonogi, and K. Itoh Chem. Pharm. Bull. 41 1993 1035
51. J.-S. Li, Y. Li, C. Son, and A.M.H. Brodie Prostate 36 1998 92