Design, synthesis, and structure-activity relationships of a series of 2-Ar-8-methyl-5-alkylaminoquinolines as novel CRF1 receptor antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 17, 2012, Pages 5372-5378

  Takeda, Kunitoshi ^a   Terauchi, Taro ^a   Hashizume, Minako ^a   Shin, Kogyoku ^a   Ino, Mitsuhiro ^a   Shibata, Hisashi ^a   Yonaga, Masahiro ^a  

^a EISAI CO LTD   (Japan)

Author keywords

Corticotropin releasing factor; Depression; Pharmacophore; Stress; Structure activity relationships

Indexed keywords

2 AR 8 METHYL 5 ALKYLAMINOQUINOLINE; 3 (6 DIMETHYLAMINO 4 METHYL 3 PYRIDINYL) 7 DIPROPYLAMINO 2,5 DIMETHYLPYRAZOLO[1,5 A]PYRIMIDINE; 8 (2,4 DICHLOROPHENYL) 4 [2 METHOXY 1 (METHOXYMETHYL)ETHYLAMINO] 2,7 DIMETHYLPYRAZOLO[1,5 A][1,3,5]TRIAZINE; BUTYL[2,5 DIMETHYL 7 (2,4,6 TRIMETHYLPHENYL) 7H PYRROLO[2,3 D]PYRIMIDIN 4 YL]ETHYLAMINE; CORTICOTROPIN RELEASING FACTOR RECEPTOR 1; CP 316311; HORMONE RECEPTOR BLOCKING AGENT; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DERIVATIZATION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ADMINISTRATION, ORAL; ANIMALS; DEPRESSION; DRUG DESIGN; HEK293 CELLS; HUMANS; MODELS, MOLECULAR; QUINOLINES; RATS; RECEPTORS, CORTICOTROPIN-RELEASING HORMONE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84865128033     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.07.047     Document Type: Article

References (22)

1. W. Vale, J. Spiess, C. Rivier, and J. Rivier Science 213 1981 1394
2. C.B. Nemeroff, E. Widerlov, G. Bissette, H. Wallens, I. Karlsson, K. Eklund, C.D. Kilts, P.T. Loosen, and W. Vale Science 226 1984 1342
3. F. Holsboer, U. Von Bardeleben, A. Gerken, G.K. Stella, and O.A. Muller N. Engl. J. Med. 311 1984 1127
4. R. Chen, K.A. Lewis, M.H. Perrin, and W.W. Vale Proc. Natl. Acad. Sci. U.S.A. 90 1993 8967
5. M.H. Perrin, C.J. Donaldoson, R. Chen, K.A. Lewis, and W.W. Vale Endocrinology 133 1993 3058
6. T.W. Lovenberg, C.W. Liaw, D.E. Grigoriadis, W. Clevenger, D.T. Chalmers, E.B. DeSouza, and T. Oltersdorf Proc. Natl. Acad. Sci. U.S.A. 92 1995 836
7. C.P. Chang, R.V. Pearse, S. O'Connell, and M.G. Rosenfeld Neuron 11 1993 1187
8. D.T. Chalmers, T.W. Lovenberg, D.E. Grigoriadis, D.P. Behan, and E.B. DeSouza Trends Pharmacol. Sci. 17 1996 166
9. M.A. Millan, D.M. Jacobowitz, R.L. Hauger, K.J. Catt, and G. Aguilera Proc. Natl. Acad. Sci. U.S.A. 83 1986 1921
10. D.E. Grigoriadis, G.W. Dent, J.G. Turner, H. Uno, S.E. Shelton, E.B. DeSouza, and N.H. Kalin Dev. Neurosci. 17 1995 357
11. C. Chen, K.M. Wilcoxen, C.Q. Huang, Y.F. Xie, J.R. McCarthy, T.R. Webb, Y.-F. Zhu, J. Saunders, X.J. Liu, T.K. Chen, H. Bozigian, and D.E. Grigoriadis J. Med. Chem. 47 2004 4787
12. D.W. Schulz, R.S. Mansbach, J. Sprouse, J.P. Braselton, J. Collins, M. Corman, A. Dunaiskis, S. Faraci, A.W. Schmidt, T. Seeger, P. Seymour, F.D. Tingley, E.N. Winston, Y.L. Chen, and J. Heym Proc. Natl. Acad. Sci. U.S.A. 93 1996 10477
13. R.S. Mansbach, E.N. Brooks, and Y.L. Chen Eur. J. Pharmacol. 323 1997 21
14. L. He, P.J. Gilligan, R. Zaczek, L.W. Fitzgerald, J.F. McElroy, H.-S.L. Shen, J.A. Saye, N.H. Kalin, S. Shelton, D. Christ, G. Trainor, and P. Hartig J. Med. Chem. 430 2000 449
15. Y.L. Chen, J. Braselton, J. Forman, R.J. Gallaschun, R. Mansbach, A.W. Schmidt, T.F. Seeger, J.S. Sprouse, F.D. Tingley, E. Winston, and D.W. Schulz J. Med. Chem. 51 2008 1377
16. Y.L. Chen, R.S. Obach, J. Braselton, M.L. Corman, J. Forman, J. Freeman, R.J. Gallaschun, R. Mansbach, A.W. Schmidt, J.S. Sprouse, F.D. Tingley, E. Winston, and D.W. Schulz J. Med. Chem. 51 2008 1385
17. A.W. Zobel, T. Nickel, H.E. Kunzel, N. Ackl, A. Sonntag, M. Ising, and F. Holsboer J. Psychiatr. Res. 34 2000 171
18. B. Binneman, D. Feltner, S. Kolluri, Y. Shi, R. Qiu, and T. Stiger Am. J. Psychiatry 165 2008 617
19. K. Takeda, T. Terauchi, K. Shin, M. Ino, H. Shibata, and M. Yonaga Bioorg. Med. Chem. 22 2012 4756
20. N. Miyaura, K. Yamada, and A. Suzuki Tetrahedron Lett. 20 1979 3437
21. E. Arzel, P. Rocca, F. Marsais, A. Godard, and G. Queguiner Tetrahedron Lett. 39 1998 6465
22. P.R. Saunders, C. Maillot, M. Million, and Y. Tache Eur. J. Pharmacol. 435 2002 231