Design, synthesis, and biological evaluation of 3-aryl-3-hydroxy-1- phenylpyrrolidine derivatives as novel androgen receptor antagonists

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 1, 2013, Pages 70-83

  Yamamoto, Satoshi ^a   Kobayashi, Hiromi ^a   Kaku, Tomohiro ^a   Aikawa, Katsuji ^a   Hara, Takahito ^a   Yamaoka, Masuo ^a   Kanzaki, Naoyuki ^a   Hasuoka, Atsushi ^a   Baba, Atsuo ^a   Ito, Mitsuhiro ^a  

^a TAKEDA PHARMACEUTICAL COMPANY LIMITED   (Japan)

Author keywords

3 Aryl 3 hydroxy 1 phenylpyrrolidine derivatives; Androgen receptor antagonists; Castration resistant prostate cancers

Indexed keywords

1 (4 CYANOPHENYL) 3 ARYL PYRROLIDINE DERIVATIVE; 1 (4 CYANOPHENYL) 3 BENZYL PYRROLIDINE DERIVATIVE; 1 (4 CYANOPHENYL) 3 HYDROXYPYRROLIDINE; 2 CHLORO 4 (2 METHYL 3 OXOPYRROLIDIN 1 YL)BENZONITRILE; 2 CHLORO 4 (3 HYDROXY 2 METHYLPYRROLIDIN 1 Y)BENZONITRILE; 2 CHLORO 4 (3 HYDROXY 3 PHENYLPYRROLIDIN 1 YL)BENZONITRILE; 2 CHLORO 4 (3 HYDROXYPYRROLIDIN 1 YL)BENZONITRILE; 2 CHLORO 4 (3 OXOPYRROLIDIN 1 YL)BENZONITRILE; 2 CHLORO 4 [3 HYDROXY 3 (4 FLUOROPHENYL) 2 METHYLPYRROLIDIN 1]BENZONITRILE; 2 METHOXY 4 (2 METHYL 3 OXOPYRROLIDIN 1 YL)BENZONITRILE; 3 ARYL 3 HYDROXY 1 PHENYLPYRROLIDINE DERIVATIVE; 4 (2 METHYL 3 OXOPYRROLIDIN 1 YL)BENZONITRILE; 4 (3 BENZYL HYDROXYPYRROLIDIN 1 YL)2 CHLOROBENZONITRILE; 4 (3 HYDROXY 2 METHYLPYRROLIDIN 1 YL) 2 METHOXYBENZONITRILE; 4 [3 (5 BROMOPYRIDIN 2 YL) 3 HYDROXY 2 METHYLPYRROLIDIN 1 YL] 2 CHLOROBENZONITRILE; 4 [3 (6 BROMOPYRIDIN 2 YL) 3 HYDROXY 2 METHYLPYRROLIDIN 1 YL] 2 CHLOROBENZONITRILE; 4 [3 (6 BROMOPYRIDIN 2 YL) 3 HYDROXY 2 METHYLPYRROLIDIN 1 YL]BENZONITRILE; ANDROGEN RECEPTOR; ANDROGEN RECEPTOR ANTAGONIST; BENZYL 3 HYDROXY 2 METHYLPYRROLIDINE 1 CARBOXYLATE; BICALUTAMIDE; ETHYL 4 [1 (3 CHLORO 4 CYANOPHENYL) 3 HYDROXY 2 METHYLPYRROLIDIN 3 YL]BENZOATE; ETHYL 5 [1 ( 4 CYANOPHENYL) 3 HYDROXY 2 METHYLPYRROLIDIN 3 YL]PYRIDINE 2 CARBOXYLATE; ETHYL 5 [1 (3 CHLORO 4 CYANOPHENYL) 3 HYDROXY 2 METHYLPYRROLIDIN 3 YL]PYRIDINE 2 CARBOXYLATE; ETHYL 5 [1 (4 CYANO 3 METHOXYPHENYL) 3 HYDROXY 2 METHYLPYRROLIDIN 3 YL]PYRIDINE 2 CARBOXYLATE; METHYL 6 [1 (3 CHLORO 4 CYANOPHENYL) 3 HYDROXY 2 METHYLPYRROLIDIN 3 YL]PYRIDINE 2 CARBOXYLATE; NEW DRUG; PROSTATE SPECIFIC ANTIGEN; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; CANCER CELL CULTURE; CASTRATION RESISTANT PROSTATE CANCER; CONTROLLED STUDY; DRUG DESIGN; DRUG EFFICACY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; EXPERIMENTAL MOUSE; HUMAN; HUMAN CELL; IC 50; MOUSE; NONHUMAN; TUMOR XENOGRAFT; WILD TYPE;

ANDROGEN RECEPTOR ANTAGONISTS; ANIMALS; ANTINEOPLASTIC AGENTS; CASTRATION; CELL LINE, TUMOR; DRUG DESIGN; HUMANS; MALE; MICE; MODELS, MOLECULAR; PROSTATE; PROSTATIC NEOPLASMS; PYRROLIDINES; RECEPTORS, ANDROGEN; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84870899439     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.11.001     Document Type: Article

References (43)

1. R.O. Neri, M.D. Monahan, J.G. Meyer, B.A. Afonso, and I.A. Tabachnick Eur. J. Pharmacol. 1 1967 438
2. R. Neri, K. Florance, P. Koziol, and S. Van Cleave Endocrinology 91 1972 427
3. F. Labrie Cancer 72 1993 3816
4. A.E. Wakeling, B.J. Furr, A.T. Glen, and L.R.J. Hughes Steroid Biochem. 15 1981 355
5. J.M. Kuhn, T. Billebaud, H. Navratil, A. Moulonguet, J. Friet, P. Grise, J.F. Louis, P. Costa, J.M. Husson, R. Dahan, C. Bertagna, and R.N. Edelstein Engl. J. Med. 321 1989 413
6. H. Tucker, and G.J. Chesterson J. Med. Chem. 31 1988 885
7. H. Tucker, J.W. Crook, and G.J. Chesterson J. Med. Chem. 31 1988 954
8. Kolvenbag, G. J.; Blackledge, G. R. Urology 1996, 47, 70; discussion 80.
9. G.J. Kolvenbag, and B.J. Furr Urology 54 1999 194
10. P.F. Schellhammer, and J.W. Davis Clin. Prostate Cancer 2 2004 213
11. Y. Fradet Expert Rev. Anticancer Ther. 4 2004 37
12. W.A. See, M.P. Wirth, D.G. McLeod, P. Iversen, I. Klimberg, D. Gleason, G. Chodak, J. Montie, C. Tyrrell, D.M.A. Wallace, K.P.J. Delaere, S. Vaage, T.L.J. Tammela, O. Lukkarinen, B.-E. Persson, K. Carrol, and G.J.C.M. Kolvenbag J. Urol. 168 2002 429
13. H. Akaza, A. Yamaguchi, T. Matsuda, M. Igawa, H. Kumon, A. Soeda, Y. Arai, M. Usami, S. Naito, H. Kanetake, and Y. Ohashi Jpn. J. Clin. Oncol. 34 2004 20
14. M.P. Wirth, W.A. See, D.G. McLeod, P. Iversen, T. Morris, and K. Carroll J. Urol. 172 2004 1865
15. P. Iversen, J.-E. Johansson, P. Lodding, O. Lukkarinen, P. Lundmo, P. Klarskov, T.L.J. Tammela, I. Tasdemir, T. Morris, and K. Carroll J. Urol. 172 2004 1871
16. F.H. Schröder Eur. Urol. 53 2008 1129
17. C.D. Chen, D.S. Welsbie, C. Tran, S.H. Baek, R. Chen, R. Vessella, M.G. Rosenfeld, and C.L. Sawyers Nat. Med. 10 2004 33
18. M. Yamaoka, T. Hara, and M. Kusaka Clin. Cancer Res. 16 2010 4319
19. M.P. Wirth, O.W. Hakenberg, and M. Froehner Eur. Urol. 51 2007 306
20. I.F. Tannock, R. de Wit, W.R. Berry, J. Horti, A. Pluzanska, K.N. Chi, S. Oudard, C. Théodore, N.D. James, I. Turesson, M.A. Rosenthal, and M.A. Eisenberger N. Engl. J. Med. 351 2004 1502
21. D. Mukherji, C.J. Pezaro, and J.S. De-Bono Expert Opin. Investig. Drugs 21 2012 227
22. J.S. de Bono, C.J. Logothetis, A. Molina, K. Fizazi, S. North, L. Chu, C.N. Chi, R.J. Jones, O.B. Goodman, F. Saad, J.N. Staffurth, P. Mainwaring, S. Harland, T.W. Flaig, T.E. Huston, T. Cheng, H. Patterson, J.D. Hainsworth, C.J. Ryan, C.N. Sternberg, S. Ellard, A. Fléchon, M. Saleh, M. Scholz, E. Efstathiou, A. Zivi, D. Bianchini, Y. Loriot, N. Chieffo, T. Kheoh, C.M. Haqq, and H.I. Scher N. Engl. J. Med. 364 2011 1995
23. M.E. Jung, S. Ouk, D. Yoo, C.L. Sawyers, C. Chen, C. Tran, and J. Wongvipat J. Med. Chem. 53 2010 2779
24. C. Tran, S. Ouk, N.J. Clegg, Y. Chen, P.A. Watson, V. Arora, J. Wongvipat, P.M. Smith-Jones, D. Yoo, A. Kwon, T. Wasielewska, D. Welsbie, C.D. Chen, C.S. Higano, T.M. Beer, D.T. Hung, H.I. Scher, M.E. Jung, and C.L. Sawyers Science 324 2009 787
25. S. Yamamoto, N. Matsunaga, T. Hitaka, M. Yamada, T. Hara, J. Miyazaki, T. Santou, M. Kusaka, M. Yamaoka, N. Kanzaki, S. Furuya, A. Tasaka, K. Hamamura, and M. Ito Bioorg. Med. Chem. 20 2012 422
26. S. Yamamoto, N. Tomita, Y. Suzuki, T. Suzaki, T. Kaku, T. Hara, M. Yamaoka, N. Kanzaki, A. Hasuoka, A. Baba, and M. Ito Bioorg. Med. Chem. 20 2012 2338
27. C. Guo, A. Linton, S. Kephart, M. Ornelas, M. Pairish, J. Gonzalez, S. Greasley, A. Nagata, B.J. Burke, M. Edwards, H. Hosea, P. Kang, W. Hu, J. Engebretsen, D. Briere, M. Shi, H. Gukasyan, P. Richardson, K. Dack, T. Underwood, P. Johnson, A. Morell, R. Felstead, H. Kuruma, H. Matsimoto, A. Zoubeid, M. Gleave, G. Los, and A.N. Fanjul J. Med. Chem. 54 2011 7693
28. R.M. Attar, M. Jure-Kunkel, A. Balog, M.E. Cvijic, J. Dell-John, C.A. Rizzo, L. Schweizer, T.E. Spires, J.S. Platero, M. Obermeier, W. Shan, M.E. Salvati, W.R. Foster, J. Dinchuk, S.J. Chen, G. Vite, R. Kramer, and M.M. Gottardis Cancer Res. 69 2009 6522
29. S. Fujii, A. Yamada, K. Tomita, M. Nagano, T. Goto, K. Ohta, T. Harayama, Y. Endo, and H. Kagechika Med. Chem. Commun. 2 2011 877
30. T. Goto, K. Ohta, S. Fujii, S. Ohta, and Y. Endo J. Med. Chem. 53 2010 4917
31. I. Kinoyama, N. Taniguchi, A. Toyoshima, E. Nozawa, T. Kamikubo, M. Imamura, A. Matsuhisa, K. Samizu, E. Kawanimani, T. Niimi, N. Hamada, H. Koutoku, T. Furutani, M. Kudoh, M. Okada, M. Ohta, and S. Tsukamoto J. Med. Chem. 49 2006 716
32. C. Guo, M. Pairish, A. Linton, S. Kephart, M. Ornelas, A. Nagata, B. Burke, L. Dong, J. Engebretsen, and A.N. Fanjul Bioorg. Med. Chem. Lett. 22 2012 2572
33. Shiraishi, M.; Hara, T.; Kusaka, M.; Kanzaki, N.; Yamamoto, S.; Miyawaki, T. EP Patent 1553074, 2005.
34. Wang, X.; Rabbat, P.; O'Shea, P.; Tillyer, R.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron Lett. 2000, 41, 4335.
35. A. Klapars, X. Huang, and S.L. Buchwald J. Am. Chem. Soc 124 2002 7421
36. T. Hara, J. Miyazaki, H. Araki, M. Yamaoka, N. Kanzaki, M. Kusaka, and M. Miyamoto Cancer Res. 63 2003 149
37. T. Ishioka, A. Tanatani, K. Nagasawa, and Y. Hashimoto Bioorg. Med. Chem. Lett. 13 2003 2655
38. Y. Hashimoto, and H. Miyachi Bioorg. Med. Chem. 13 2005 5080
39. K. Tachibana, I. Imaoka, T. Shiraishi, H. Yoshino, M. Nakamura, M. Ohta, H. Kawata, K. Taniguchi, N. Ishikura, T. Tsunenari, H. Saito, M. Nagamuta, T. Nakagawa, K. Takanashi, E. Onuma, and H. Sato Chem. Pharm. Bull. 56 2008 1555
40. H. Yoshino, H. Sato, K. Tachibana, T. Shiraishi, M. Nakamura, M. Ohta, N. Ishikura, M. Nagamuta, E. Onuma, T. Nakagawa, S. Arai, K.-H. Ahn, K.-Y. Jung, and H. Kawata Bioorg. Med. Chem. 18 2010 3159
41. D. McKillop, G.W. Boyle, I.D. Cockshott, D.C. Jones, P.J. Phillips, and R.A. Yates Xenobiotica 23 1993 1241
42. H.D. Flack Acta Crystallogr. A 39 1983 876
43. R.W. Boesel, and S.A. Shain Biochem. Biophys. Res. Commun. 61 1974 1004