Fragment-based discovery of 6-substituted isoquinolin-1-amine based ROCK-I inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 1, 2011, Pages 97-101

  Ray, Peter ^a   Wright, Jane ^a   Adam, Julia ^a   Bennett, Johnathan ^a   Boucharens, Sylviane ^a   Black, Darcey ^a   Cook, Andrew ^a   Brown, Angus R ^a   Epemolu, Ola ^a   Fletcher, Dan ^a   Haunso, Anders ^a   Huggett, Margaret ^a   Jones, Phil ^a   Laats, Steven ^a   Lyons, Amanda ^a   Mestres, Jordi ^a   De Man, Jos ^a   Morphy, Richard ^a   Rankovic, Zoran ^a   Sherborne, Brad ^a   Sherry, Lorcan ^a   Van Straten, Nicole ^a   Westwood, Paul ^a   Zaman, Guido Z R ^a   more..

^a MSD   (United Kingdom)

Author keywords

FBDD; Fragment based drug discovery; Rho kinase; ROCK inhibitors; ROCK I; STD NMR

Indexed keywords

4 (1 AMINOETHYL) N (4 PYRIDYL)CYCLOHEXANECARBOXAMIDE; FASUDIL; ISOQUINOLINE DERIVATIVE; RHO KINASE INHIBITOR;

ANIMAL EXPERIMENT; ARTICLE; BINDING AFFINITY; DRUG BIOAVAILABILITY; DRUG EFFICACY; DRUG POTENCY; DRUG SYNTHESIS; IC 50; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; RAT;

AMINES; ANIMALS; BINDING SITES; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; DRUG EVALUATION, PRECLINICAL; ISOQUINOLINES; MICE; MICE, INBRED C57BL; PROTEIN KINASE INHIBITORS; RHO-ASSOCIATED KINASES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 78650513427     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.11.060     Document Type: Article

References (34)

1. M. Amano, Y. Fukata, and K. Kaibuchi Exp. Cell Res. 261 2000 44
2. K. Riento, and A.J. Ridley Nat. Rev. Mol. Cell Biol. 4 2003 446
3. M. Schwartz J. Cell Sci. 117 2004 5457
4. P.V. LoGrasso, and Y. Feng Curr. Top. Med. Chem. 9 2009 704
5. K. Noma, N. Oyama, and J.K. Liao Am. J. Physiol. Cell Physiol. 290 2006 C661
6. H. Saito, Y. Minamiya, S. Saito, and J. Ogawa J. Leukoc. Biol. 72 2002 829
7. Y. Kawano, T. Yoshimura, and K. Kaibuchi J. Med. Sci. 65 2002 1
8. J. Shi, and L. Wei Arch. Immunol. Ther. Exp. 55 2007 61
9. Y.T. Shiu, S. Li, W.A. Marganski, S. Usami, M.A. Schwartz, Y.L. Wang, M. Dembo, and S. Chien Biophys. J. 86 2004 2558
10. K. Budzyn, P.D. Marley, and C.G. Sobey TIPS 27 2006 97
11. M. Dong, B.P. Yan, J.K. Liao, Y.Y. Lam, G.W. Yip, and C.M. Yu Drug Discovery Today 15 2010 622
12. E. Hu, and D. Lee Expert Opin. Ther. Targets 9 2005 715
13. A. Lai, and W.H. Frishman Cardiol. Rev. 13 2005 285
14. T.M. Seasholtz, and J.H. Brown Mol. Interv. 4 2004 348
15. Boyce-Rustay, J. M.; Simler, G. H.; McGaraughty, S.; Chu, K. L.; Wensink, E. J.; Vasudevan, A.; Honore, P. J. Pain. 2010 Mar 23 [Epub ahead of print].
16. K. Büyükafar, I. Yalin, A.H. Kurt, R.N. Tiftik, S. Sahan-Firat, and F. Aksu Eur. J. Pharmacol. 10 2006 49
17. T. Kubo, A. Yamaguchi, N. Iwata, and T. Yamashita Ther. Clin. Risk Manag. 4 2008 605
18. S. Micuda, D. Rösel, A. Ryska, and J. Brábek Curr. Cancer Drug Targets 1 2010 127
19. B.K. Mueller, H. Mack, and N. Teusch Nat. Rev. Drug Discov. 4 2005 387
20. M.F. Olson Curr. Opin. Cell Biol. 20 2008 242
21. B.L. Tang, and Y.C. Liou J. Neurochem. 100 2007 314
22. B.K. Mueller, H. Mack, and N. Teusch Nat. Rev. Drug Discov. 4 2005 387
23. R.A. Stavenger, H. Cui, S.E. Dowdell, R.G. Franz, D.E. Gaitanopoulos, K.B. Goodman, M.A. Hilfiker, R.L. Ivy, J.D. Leber, J.P. Marino Jr., H.-J. Oh, A.Q. Viet, W. Xu, G. Ye, D. Zhang, Y. Zhao, L.J. Jolivette, M.S. Head, S.F. Semus, P.A. Elkins, R.B. Kirkpatrick, E. Dul, S.S. Khandekar, T. Yi, D.K. Jung, L.L. Wright, G.K. Smith, D.J. Behm, C.P. Doe, R. Bentley, Z.X. Chen, E. Hu, and D. Lee J. Med. Chem. 50 2007 2
24. K.B. Goodman, H. Cui, S.E. Dowdell, D.E. Gaitanopoulos, R.L. Ivy, C.A. Sehon, R.A. Stavenger, G.Z. Wang, A.Q. Viet, W. Xu, G. Ye, S.F. Semus, C. Evans, H.E. Fries, L.J. Jolivette, R.B. Kirkpatrick, E. Dul, S.S. Khandekar, T. Yi, D.K. Jung, L.L. Wright, G.K. Smith, D.J. Behm, R. Bentley, C.P. Doe, E. Hu, and D. Lee J. Med. Chem. 50 2007 6
25. M. Congreve, G. Chessari, D. Tisi, and A.J. Woodhead J. Med. Chem. 51 2008 3661
26. A. Takami, M. Iwakubo, Y. Okada, T. Kawata, H. Odai, N. Takahashi, K. Shindo, K. Kimura, Y. Tagami, M. Miyake, K. Fukushima, M. Inagaki, M. Amano, K. Kaibuchi, and H. Iijima Bioorg. Med. Chem. 12 2004 2115
27. J.B.M. Rewinkel, H. Lucas, P.J.M. Van Galen, A.B.J. Noach, T.G. Van Dinther, A.M.M. Rood, A.J.S.M. Jenneboer, and C.A.A. Van Boeckel Bioorg. Med. Chem. Lett. 9 1999 685
28. Van Boeckel, C. A. A.; Van Galen, P. J. M.; Rewinkel, J. B. M. WO 9847876 A1.
29. J.I. Trujillo, H.-C. Huang, W.L. Neumann, M.W. Mahoney, S. Long, W. Huang, D.J. Garland, C. Kusturin, Z. Abbas, M.S. South, and D.B. Reitz Bioorg. Med. Chem. Lett. 17 2007 4568
30. Registered trademark of Molecular Devices. J.R. Sportsman, E.A. Gaudet, and A. Boge Assay Drug Dev. Technol. 2 2004 205
31. A. Takami, M. Iwakubo, Y. Okada, T. Kawata, H. Odai, N. Takahashi, K. Shindo, K. Kimura, Y. Tagami, M. Miyake, K. Fukushima, M. Inagaki, M. Amano, K. Kaibuchi, and H. Iijima Bioorg. Med. Chem. 12 2004 2115
32. The study was conducted in 2004. ROCK inhibitors bound to PKA were also reported: C. Breitenlechner, M. Gassel, H. Hidaka, V. Kinzel, R. Huber, R.A. Engh, and Bossemeyer Structure 11 2003 1595
33. A ROCK crystal structure was published in 2006: M. Jacobs, K. Hayakawa, L. Swenson, S. Bellon, M. Fleming, P. Taslimi, and J.J. Doran Biol. Chem. 281 2006 260
34. P. Traxler, and P. Furet Phamacol. Ther. 82 1999 195