Synthesis and structure-activity relationship of aminopyridines with substituted benzoxazoles as c-Met kinase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 12, 2012, Pages 4044-4048

  Lee, Jongkook ^a,b   Han, Sun Young ^a,c   Jung, Heejung ^a   Yang, Jeon ^a,d   Choi, Jie Won ^a,e   Chae, Chong Hack ^a   Park, Chi Hoon ^a   Choi, Sang Un ^a   Lee, Kwangho ^a   Ha, Jae Du ^a   Lee, Chong Ock ^a   Ryu, Jae Wook ^a   Kim, Hyoung Rae ^a   Koh, Jong Sung ^a   Cho, Sung Yun ^a  

^a Korea Research Institute of Chemical Technology   (South Korea)

^b Kangwon National University   (South Korea)

^c Gyeongsang National University   (South Korea)

^d Chungnam National University   (South Korea)

^e Sogang University   (South Korea)

Author keywords

Aminopyridine; Benzoxazole; c Met kinase; Cancer

Indexed keywords

BENZOXAZOLE DERIVATIVE; CYTOKINE RECEPTOR ANTAGONIST; HYDROXYBENZOXAZOLE DERIVATIVE; HYDROXYL GROUP; SCATTER FACTOR RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; STRUCTURE ACTIVITY RELATION;

AMINOPYRIDINES; ANTINEOPLASTIC AGENTS; BENZOXAZOLES; CELL LINE, TUMOR; CELL PROLIFERATION; COMPUTER SIMULATION; FMS-LIKE TYROSINE KINASE 3; HUMANS; MODELS, MOLECULAR; PROTO-ONCOGENE PROTEINS C-MET; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84861579833     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.04.083     Document Type: Article

References (29)

1. W.G. Jiang, T.A. Martin, C. Parr, G. Davies, K. Matsumoto, and T. Nakamura Crit. Rev. Oncol. Hematol. 53 2005 35
2. L. Trusolino, A. Bertotti, and M.P. Comoglio Nat. Rev. Mol. Cell Biol. 11 2010 834
3. J.P. Eder, G.F. VandeWoude, S.A. Boerner, and P.M. LoRusso Clin. Cancer Res. 15 2009 2207
4. X. Liu, W. Yao, R.C. Newton, and P. Scherle Expert Opin. Investig. Drugs 17 2008 997
5. N. Puri, S. Ahmed, V. Janamanchi, M. Tretiadova, O. Zumba, T. Krausz, R. Jagadeeswaran, and R. Salgia Clin. Cancer Res. 13 2007 2246
6. C. Birchmerier, W. Birchmerier, E. Gherardi, and G.F. Vande Woude Nat. Rev. Mol. Cell Biol. 4 2003 915
7. B. Peruzzi, and D. Bottaro Clin Cancer Res. 12 2006 3657
8. A.Z. Lai, J.V. Abella, and M. Park Trends Cell Biol. 19 2009 542
9. C.F. Gao, and G.F. Vande Woude Cell Res. 15 2005 49
10. L. Trusolino, and P.M. Comoglio Nat. Rev. Cancer 2 2003 289
11. S. Corso, C. Migliore, E. Ghiso, G.D. Rosa, P.M. Comoglio, and S. Giordano Oncogene 27 2008 684
12. E. Lensgyel, K. Sawada, and R. Salgia Curr. Mol. Med. 7 2007 77
13. P.C. Ma, M.S. Tretiakova, B. Nallasura, R. Jagadeeswaran, A.N. Husain, and R. Salgia Br. J. Cancer 97 2007 368
14. A. Benvenuti, and P.M. Comoglio J. Cell Physiol. 213 2007 316
15. J. Christensen, J. Burrow, and R. Salgia Cancer Lett. 225 2005 1
16. J. Qi, M.A. Mctigue, A. Rogers, E. Fifshits, J.G. Christensen, P.A. Jannne, and J.A. Engelman Cancer Res. 71 2011 1081
17. L. Liu, H. Shi, and Y. Liu Mol. Cancer Ther. 10 2011 518
18. V. Cepero, J.R. Sierra, S. Corso, E. Hhiso, L. Casorzo, T. Perera, P.M. Comoglio, and S. Giordano Cancer Res. 70 2010 7580
19. J. Bean, C. Brennan, J.-Y. Shih, G. Riely, A. Viale, L. Wang, D. Shitale, N. Motoi, J. Szoke, S. Broderick, M. Balak, W.-C. Chang, C.-J. Yu, A. Gazdar, H. Pass, V. Rusch, W. Gerald, S.-F. Huang, P.-C. Yang, V. Miller, M. Ladanyi, C.-H. Yang, and W. Pao Proc. Natl. Acad. Sci. U.S.A. 26 2007 20932
20. S.Y. Cho, S.Y. Han, J.D. Ha, J.W. Ryu, J.O. Lee, H. Jung, N.S. Kang, H.R. Kim, J.S. Koh, and J. Lee Bioorg. Med. Chem. Lett. 20 2010 4223
21. S.-Y. Han, J.O. Lee, S.-H. Ahn, M.-O. Lee, S.-Y. Kang, H.-J. Cha, S.Y. Cho, J.D. Ha, J.W. Ryu, H.J. Jung, H.R. Kim, J.S. Koh, and J. Lee Invest. New Drugs 30 2012 518
22. T. Satoh, Y. Kawamura, M. Miura, and M. Nomura Angew. Chem., Int. Ed. 36 1997 1740
23. R.A. Friesner, J.L. Banks, R.B. Murphy, T.A. Halgren, J.J. Klicic, and D.T. Mainz J. Med. Chem. 47 2004 1739
24. J. Porter, S. Lumb, F. Lecomte, J. Reuberson, A. Foley, M. Calmiano, K. le Riche, H. Edwards, J. Delgado, R.J. Franklin, J.M. Gascon-Simorte, A. Maloney, C. Meier, and M. Batchelor Bioorg. Med. Chem. Lett. 19 2009 397
25. D. Schmidt-Arras, J. Schwable, F.D. Bohmer, and H. Serve Curr. Pharm. Des. 2004 1867 10
26. H. Reeger, J.-M. Rondeau, C. McCarthy, H. Movitz, M. Tintelnot-Blomley, U. Neumann, and S. Desrayaud Bioorg. Med. Chem. Lett. 2011 1942 12
27. C.M. Shafer, M. Lindvall, C. Bellamachina, T.G. Gesner, A. Yabannavar, W. Jia, S. Lin, and A. Walter Bioorg. Med. Chem. Lett. 18 2008 4482
28. P. Bamborough, R.M. Amgell, I. Bhamra, D. Brown, J. Bull, J.A. Christopher, A.W. Cooper, L.H. Fazal, I. Giordano, L. Hind, V.K. Patel, L.E. Ranshaw, M.J. Sims, P.A. Akone, K.J. Smith, E. Vickerstaff, and M. Washington Bioorg. Med. Chem. Lett. 17 2007 4363
29. N. Diaz, M. Benvenga, P. Emmerson, R. Ravors, M. Mangold, J. Mckinzie, N. Patel, S. Peters, S. Quimby, H. Shannon, S. Miles, M. Statnick, E. Thomas, J. Woodland, P. Surface, and C. Mitch Bioorg. Med. Chem. Lett. 15 2005 3844