Design and synthesis of triazolopyridazines substituted with methylisoquinolinone as selective c-Met kinase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 23, 2011, Pages 7185-7188

  Ryu, Jae Wook ^a   Han, Sun Young ^a,b   Yun, Jeong In ^a,c   Choi, Sang Un ^a   Jung, Heejung ^a   Ha, Jae Du ^a   Cho, Sung Yun ^a   Lee, Chong Ock ^a   Kang, Nam Sook ^a,c   Koh, Jong Sung ^a   Kim, Hyoung Rae ^a   Lee, Jongkook ^a  

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

^b Gyeongsang National University   (South Korea)

^c Chungnam National University   (South Korea)

Author keywords

c Met; Cancer; Kinase inhibitor; Methylisoquinolinone; Triazolopyridazine

Indexed keywords

ANTINEOPLASTIC AGENT; METHYLISOQUINOLINONE; TRIAZOLOPYRIDAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CELL PROLIFERATION; DRUG ABSORPTION; DRUG DESIGN; DRUG ELIMINATION; DRUG STRUCTURE; DRUG SUBSTITUTION; DRUG SYNTHESIS; ENZYME INHIBITION; STOMACH CANCER; STRUCTURE ACTIVITY RELATION;

ANIMALS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG DESIGN; ENZYME ACTIVATION; HUMANS; INHIBITORY CONCENTRATION 50; ISOQUINOLINES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN KINASE INHIBITORS; PROTO-ONCOGENE PROTEINS C-MET; PYRIDAZINES; RATS; STOMACH NEOPLASMS; TRIAZOLES;

EID: 80255138845     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.09.066     Document Type: Article

References (25)

1. Z.A. Knight, H. Lin, and K.M. Shokat Nat. Rev. Cancer 10 2010 130
2. P.A. Jänne, N. Gray, and J. Settleman Nat. Rev. Drug Disc. 8 2009 709
3. J.G. Christensen, J. Burrows, and R. Salgia Cancer Lett. 225 2005 1
4. P.M. Comoglio, S. Giordano, and L. Trusolino Nat. Rev. Drug Disc. 7 2008 504
5. M. Sattler, R. Hasina, M.M. Reddy, T. Gangadhar, and R. Salgia Ther. Adv. Med. Oncol. 3 2011 171
6. T.L. Underiner, T. Herbertz, and S.J. Miknyoczki Anti-Cancer Agents Med. Chem. 10 2010 7
7. W.G. Jiang, T.A. Martin, C. Parr, G. Davies, K. Matsumoto, and T. Nakamura Crit. Rev. Oncol. Hematol. 53 2005 35
8. Zhang, F.-J.; Vojkovsky, T.; Huang, P.; Liang, C.; Do, S. H.; Koenig, M.; Cui, J. WO2005010005, 2005.
9. B.K. Albrecht, J.-C. Harmange, D. Bauer, L. Berry, C. Bode, A.A. Boezio, A. Chen, D. Choquette, I. Dussault, C. Fridrich, S. Hirai, D. Hoffman, J.F. Larrow, P. Kaplan-Lefko, J. Lin, J. Lohman, A.M. Long, J. Moriguchi, A. O'Connor, M.H. Potashman, M. Reese, K. Rex, A. Siegmund, K. Shah, R. Shimanovich, S.K. Springer, Y. Teffera, Y. Yang, Y. Zhang, and S.F. Bellon J. Med. Chem. 51 2008 2879
10. A.A. Boezio, L. Berry, B.K. Albrecht, D. Bauer, S.F. Bellon, C. Bode, A. Chen, D. Choquette, I. Dussault, S. Hirai, P. Kaplan-Lefko, J.F. Larrow, M.-H.J. Lin, J. Lohman, M.H. Potashman, K. Rex, M. Santostefano, K. Shah, R. Shimanovich, S.K. Springer, Y. Teffera, Y. Yang, Y. Zhang, and J.-C. Harmange Bioorg. Med. Chem. Lett. 19 2009 6307
11. S.G. Buchanan, J. Hendle, P.S. Lee, C.R. Smith, P.-Y. Bounaud, K.A. Jessen, C.M. Tang, N.H. Huser, J.D. Felce, K.J. Froning, M.C. Peterman, B.E. Aubol, S.F. Gessert, J.M. Sauder, K.D. Schwinn, M. Russell, I.A. Rooney, J. Adams, B.C. Leon, T.H. Do, J.M. Blaney, P.A. Sprengeler, D.A. Thompson, L. Smyth, L.A. Pelletier, S. Atwell, K. Holme, S.R. Wasserman, S. Emtage, S.K. Burley, and S.H. Reich Mol. Cancer Ther. 8 2009 3181
12. Lu, T.; Alexander, R.; Connors, R. W.; Cummings, M. D.; Galemmo, R.; Hufnagel, H. R.; Johnson, D. L.; Khalil, E.; Leonard, K. A.; Markotan, T. P.; Maroney, A. C.; Sechler, J. L.; Travins, J. M.; Tuman, R. W. WO2007075567, 2007.
13. S.L. Timofeevski, M.A. McTigue, K. Ryan, J. Cui, H.Y. Zou, J.X. Zhu, F. Chau, G. Alton, S. Karlicek, J.G. Christensen, and B.W. Murray Biochemistry 48 2009 5339
14. S. Diamond, J. Boer, T.P. Maduskuie Jr., N. Falahatpisheh, Y. Li, and S. Yeleswaram Drug Metab. Dispos. 38 2010 1277
15. S.Y. Cho, S.-Y. Han, J.D. Ha, J.W. Ryu, C.O. Lee, H. Jung, N.S. Kang, H.R. Kim, J.S. Koh, and J. Lee Bioorg. Med. Chem. Lett. 20 2010 4223
16. Han, S.-Y.; Lee, C. O.; Ahn, S.-H.; Lee, M.-O.; Kang, S.-Y.; Cha, H.-J.; Cho, S. Y.; Ha, J. D.; Ryu, J. W.; Jung, H.; Kim, H. R.; Koh, J. S.; Lee, J. Invest. New Drugs in press. doi:10.1007/s10637-010-9584-2.
17. S. Kawata, S. Ashizawa, and M. Hirama J. Am. Chem. Soc. 119 1997 12012
18. N. Briet, M.H. Brookes, R.J. Davenport, F.C.A. Galvin, P.J. Gilbert, S.R. Mack, and V. Sabin Tetrahedron 58 2002 5761
19. A.E. Thomson, G. Hughes, A.S. Batsanov, M.R. Bryce, P.R. Parry, and B. Tarbit J. Org. Chem. 70 2005 388
20. +) 353.1277, found 353.1282.
21. D.J. Diller, and M.L. Merz III Proteins: Structure, Function, and Genetics 43 2001 113
22. H. Kuniyasu, W. Yasui, Y. Kitadai, H. Yokozaki, H. Ito, and E. Tahara Biochem. Biophys. Res. Commun. 189 1992 227
23. G.A. Smolen, R. Sordella, B. Muir, G. Mohapatra, A. Barmettler, H. Archibald, W.J. Kim, R.A. Okimoto, D.W. Bell, D.C. Sgroi, J.G. Christensen, and J. Settleman Proc. Natl. Acad. Sci. U.S.A. 103 2006 2316
24. Y. Asaoka, M. Tada, T. Ikenoue, M. Seto, M. Imai, K. Miyabayashi, K. Yamamoto, S. Yamamoto, Y. Kudo, D. Mohri, Y. Isomura, H. Ijichi, K. Tateishi, F. Kanai, S. Ogawa, M. Omata, and K. Koike Biochem. Biophys. Res. Commun. 394 2010 1042
25. G. Rege-Cambrin, P. Scaravaglio, F. Carozzi, C. Ponzetto, P.M. Comoglio, and G. Saglio Cancer Genet. Cytogenet. 64 1992 170