4-([1,2,4]Triazolo[1,5-a]pyridin-6-yl)-5(3)-(6-methylpyridin-2-yl)imidazole and -pyrazole derivatives as potent and selective inhibitors of transforming growth factor-β type i receptor kinase

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 9, 2014, Pages 2724-2732

  Jin, Cheng Hua ^a   Krishnaiah, Maddeboina ^a   Sreenu, Domalapally ^a   Subrahmanyam, Vura Bala ^a   Park, Hyun Ju ^b   Park, So Jung ^b   Sheen, Yhun Yhong ^a   Kim, Dae Kee ^a  

^a Ewha Womans University   (South Korea)

^b Sungkyunkwan University   (South Korea)

Author keywords

ALK5 inhibitor; Cancer; Cell based luciferase reporter assay; Docking; Fibrosis; Kinase assay; TGF

Indexed keywords

IMIDAZOLE; IMIDAZOLE DERIVATIVE; PROTEIN BINDING; PROTEIN KINASE INHIBITOR; PROTEIN SERINE THREONINE KINASE; PYRAZOLE; PYRAZOLE DERIVATIVE; TGF-BETA TYPE I RECEPTOR; TRANSFORMING GROWTH FACTOR BETA RECEPTOR;

ANTAGONISTS AND INHIBITORS; BINDING SITE; CELL LINE; CHEMISTRY; ENZYME ACTIVE SITE; HUMAN; METABOLISM; MOLECULAR DOCKING; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

BINDING SITES; CATALYTIC DOMAIN; CELL LINE; HUMANS; IMIDAZOLES; MOLECULAR DOCKING SIMULATION; PROTEIN BINDING; PROTEIN KINASE INHIBITORS; PROTEIN-SERINE-THREONINE KINASES; PYRAZOLES; RECEPTORS, TRANSFORMING GROWTH FACTOR BETA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84899455861     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.03.022     Document Type: Article

References (49)

1. C.H. Heldin, K. Miyazono, and P. Ten Dijke Nature 390 1997 465
2. R. Derynck, and Y.E. Zhang Nature 425 2003 577
3. W. Wang, V. Koka, and H.Y. Lan Nephrology 10 2005 48
4. H. Lim, and Y.Z. Zhu Cell. Mol. Life Sci. 63 2006 2584
5. L. Gu, Y.-J. Zhu, X. Yang, Z.-J. Guo, W.-B. Xu, and X.-L. Tian Acta Pharmacol. Sin. 28 2007 382
6. F.W. Shek, and R.C. Benyon Eur. J. Gastroenterol. Hepatol. 16 2004 123
7. B. Bierie, and H.L. Moses Nat. Rev. Cancer 6 2006 506
8. S.G. Rane, J.-H. Lee, and H.-M. Lin Cytokine Growth Factor Rev. 17 2006 107
9. M. Dong, and G.C. Blobe Blood 107 2006 4589
10. S.D. Byfield, C. Major, N.J. Laping, and A.B. Roberts Mol. Pharmacol. 65 2004 744
11. A.C. De Gouville, V. Boullay, G. Krysa, J. Pilot, J.M. Brusq, F. Loriolle, J.M. Gauthier, S.A. Papworth, A. Laroze, F. Gellibert, and S. Huet Br. J. Pharmacol. 145 2005 166
12. M. Uhl, S. Aulwurm, J. Wischhusen, M. Weiler, J.Y. Ma, R. Almirez, R. Mangadu, Y.-W. Liu, M. Platten, U. Herrlinger, A. Murphy, D.A. Wong, W. Wick, L.S. Higgins, and M. Weller Cancer Res. 64 2004 7954
13. L. Bueno, D.P. de Alwis, C. Pitou, J. Yingling, M. Lahn, S. Glatt, and I. Troconiz Eur. J. Cancer 44 2008 142
14. E. Calvo-Aller, J. Baselga, S. Glatt, A. Claverly, M. Lahn, C.L. Arteaga, M.L. Rothenberg, and M.A. Carducci J. Clin. Oncol. 26 2008 14554
15. D.-K. Kim, J. Kim, and H.-J. Park Bioorg. Med. Chem. 12 2004 2013
16. D.-K. Kim, J. Kim, and H.-J. Park Bioorg. Med. Chem. Lett. 14 2004 2401
17. D.-K. Kim, Y. Jang, H.S. Lee, H.-J. Park, and J. Yoo J. Med. Chem. 50 2007 3143
18. D.-K. Kim, J.H. Choi, Y.J. An, and H.S. Lee Bioorg. Med. Chem. Lett. 18 2008 2122
19. Kim, D.-K.; Bang, Y.-J.; Kim, H.-T.; Cho, I.-S.; Park, M.-S.; An, Y. J. U.S. Patent 7,407,958 B2, 2008.
20. D.-K. Kim, S.H. Jung, H.S. Lee, and P.M. Dewang Eur. J. Med. Chem. 44 2009 568
21. P.M. Dewang, and D.-K. Kim Bioorg. Med. Chem. Lett. 20 2010 4228
22. D.-K. Kim, Y.-I. Lee, Y.W. Lee, P.M. Dewang, Y.Y. Sheen, Y.W. Kim, H.-J. Park, J. Yoo, H.S. Lee, and Y.-K. Kim Bioorg. Med. Chem. 18 2010 4459
23. C.H. Jin, M. Krishnaiah, D. Sreenu, K.S. Rao, V.B. Subrahmanyam, C.-Y. Park, J.-Y. Son, Y.Y. Sheen, and D.-K. Kim Bioorg. Med. Chem. 19 2011 2633
24. C.H. Jin, D. Sreenu, M. Krishnaiah, V.B. Subrahmanyam, K.S. Rao, A.V.N. Mohan, C.-Y. Park, J.-Y. Son, D.-H. Son, H.-J. Park, Y.Y. Sheen, and D.-K. Kim Eur. J. Med. Chem. 46 2011 3917
25. C.H. Jin, M. Krishnaiah, D. Sreenu, V.B. Subrahmanyam, K.S. Rao, A.V.N. Mohan, C.-Y. Park, J.-Y. Son, Y.Y. Sheen, and D.-K. Kim Bioorg. Med. Chem. Lett. 21 2011 6049
26. Kim, D.-K.; Sheen, Y. Y. Jin, C. H.; Park, C.-Y.; Sreenu, D.; Rao, K. S.; Krishnaiah, M.; Subrahmanyam, V. B. U.S. Patent 8,080,568 B1, 2011.
27. M. Krishnaiah, C.H. Jin, D. Sreenu, V.B. Subrahmanyam, K.S. Rao, D.-H. Son, H.-J. Park, S.W. Kim, Y.Y. Sheen, and D.-K. Kim Eur. J. Med. Chem. 57 2012 74
28. C.I. Galarreta, B.A. Thornhill, M.S. Forbes, L.N. Simpkins, D.-K. Kim, and R.L. Chevalier Am. J. Physiol. Renal Physiol. 304 2013 F481
29. J.-A. Moon, H.-T. Kim, I.-S. Cho, Y.Y. Sheen, and D.-K. Kim Kidney Int. 70 2006 1234
30. J. Luo, P.P. Ho, M.S. Buckwalter, T. Hsu, L.Y. Lee, H. Zhang, D.-K. Kim, S.-J. Kim, S.S. Gambhir, L. Steinman, and T. Wyss-Coray J. Clin. Invest. 117 2007 3306
31. J.-K. Ryu, S. Piao, H.-Y. Shin, M.J. Choi, L.W. Zhang, H.-R. Jin, W.J. Kim, J.-Y. Han, S.S. Hong, S.H. Park, S.-J. Lee, I.-H. Kim, C.R. Lee, D.-K. Kim, M. Mamura, S.-J. Kim, and J.-K. Suh J. Sex. Med. 6 2009 1284
32. G.T. Lee, J.H. Hong, T.J. Mueller, J.A. Watson, C. Kwak, Y.Y. Sheen, D.-K. Kim, S.J. Kim, and I.Y. Kim J. Urol. 180 2008 2660
33. L. Long, A. Crosby, X. Yang, M. Southwood, P.D. Upton, D.-K. Kim, and N.W. Morrell Circulation 119 2009 566
34. J.H. Kim, H.-Y. Song, J.-H. Park, H.-J. Yoon, H.G. Park, and D.-K. Kim Radiology 255 2010 75
35. H.-J. Yoon, H.-Y. Song, J.H. Kim, K.-S. Hong, Y.J. Kim, H.G. Park, and D.-K. Kim J. Vasc. Interv. Radiol. 22 2011 1321
36. A. Katre, C. Ballinger, H. Akhter, M. Fanucchi, D.-K. Kim, E. Postlethwait, and R.-M. Liu Inhalation Toxicol. 23 2011 486
37. Y.W. Kim, Y.K. Kim, J.Y. Lee, K.T. Chang, H.J. Lee, D.-K. Kim, and Y.Y. Sheen Xenobiotica 38 2008 325
38. Jin, C. H.; Krishnaiah, M.; Sreenu, D.; Subrahmanyam, V. B.; Rao, K. S.; Lee, H. W.; Park, S.-J.; Park, H.-J.; Lee, K.; Sheen, Y. Y.; Kim, D.-K. unpublished results.
39. Lee, W.-C.; Sun, L.; Feng, S.; Claudio, C.; Zhongli, Z.; Russell, C. P.; WO 2003/087304 A2, 2003; PCT Int. Appl. 2003.
40. Lee, W.-C.; Chuaqui, C.; Sun, L.; Hoemann, M.; Niu, D.; Yan, D.; Bonafoux, D.; Cornebise, M. WO 2007/076127 A2, 2007; PCT Int. Appl. 2007.
41. E.B. Veale, J.E. O'Brien, T. McCable, and T. Gunnlaugsson Tetrahedron 64 2008 6794
42. Sun, L.; Niu, D.; Shan, F.; Lee, W.-C.; Feng, X. WO 2009/009059 A1, 2009; PCT Int. Appl. 2009.
43. G.B. Pier, P. Delia, A.T. Mojgan, F. Francesca, S. Giulia, B. Stefania, R. Romeo, R.M. Allan, G. Stefania, V. Katia, and A.B. Pier Bioorg. Med. Chem. 15 2007 2514
44. S.J. Gu, J.K. Lee, A.N. Pae, H.J. Chung, H. Rhim, S.Y. Han, S.-J. Min, and Y. Cho Bioorg. Med. Chem. Lett. 20 2010 2705
45. L. Zhang, H. Li, Q. Zhu, J. Liu, L. Chen, Y. Leng, H. Jiang, and H. Liu Bioorg. Med. Chem. 17 2009 7301
46. J.L. Wrana, L. Attisano, J. Carcamo, A. Zentella, J. Doody, M. Laiho, and X.F. Wang J. Massague, Cell 71 1992 1003
47. P.A. Eyers, M. Craxton, N. Morrice, P. Cohen, and M. Goedert Chem. Biol. 5 1998 321
48. F. Gellibert, J. Woolven, M.H. Fouchet, N. Mathews, H. Goodland, V. Lovegrove, A. Laroze, V.-L. Nguyen, S. Sautet, R. Wang, C. Janson, W. Smith, G. Krysa, V. Boullay, A.-C. de Gouville, S. Huet, and D. Hartley J. Med. Chem. 47 2004 4494
49. Sybyl, x 2.0 ed.; SYBYL molecular modeling software, Tripos Inc.: St. Louis, MO, 2008.