Design, synthesis and structure-activity relationships of novel biarylamine-based Met kinase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 9, 2010, Pages 2998-3002

  Williams, David K ^a   Chen, Xiao Tao ^a   Tarby, Christine ^a   Kaltenbach, Robert ^a   Cai, Zhen Wei ^a   Tokarski, John S ^a   An, Yongmi ^a   Sack, John S ^a   Wautlet, Barri ^a   Gullo Brown, Johnni ^a   Henley, Benjamin J ^a   Jeyaseelan, Robert ^a   Kellar, Kristen ^a   Manne, Veeraswamy ^a   Trainor, George L ^a   Lombardo, Louis J ^a   Fargnoli, Joseph ^a   Borzilleri, Robert M ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

c Met kinase inhibitor; HGFR inhibitor; Kinase inhibitor; Met kinase

Indexed keywords

ANTINEOPLASTIC AGENT; MET KINASE INHIBITOR; PHOSPHOTRANSFERASE INHIBITOR; SCATTER FACTOR RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CARCINOMA CELL; CONTROLLED STUDY; DOSE RESPONSE; DRUG DESIGN; DRUG IDENTIFICATION; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVITY; HUMAN; HUMAN CELL; IN VIVO STUDY; MAXIMUM PLASMA CONCENTRATION; MOUSE; NONHUMAN; PROTEIN DOMAIN; STOMACH CARCINOMA; STRUCTURE ACTIVITY RELATION; TUMOR XENOGRAFT; X RAY CRYSTALLOGRAPHY;

AMINES; AMINOPYRIDINES; ANTINEOPLASTIC AGENTS; BINDING SITES; CELL LINE, TUMOR; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; HUMANS; PROTEIN KINASE INHIBITORS; PROTO-ONCOGENE PROTEINS C-MET; STRUCTURE-ACTIVITY RELATIONSHIP; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 77950863993     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.01.042     Document Type: Article

References (20)

1. For recent reviews on Met kinase see:. Migliore C., and Giordano S. Eur. J. Cancer 44 (2008) 641
2. Peruzzi B., and Bottaro D.P. Clin. Cancer Res. 12 (2006) 3657
3. Christensen J.G., Burrows J., and Salgia R. Cancer Lett. 225 (2005) 1
4. Ma P.C., Maulik G., Christensen J., and Salgia R. Cancer Metastasis Rev. 22 (2003) 309
5. Maulik G., Shrikhande A., Kijima T., Ma P.C., Morrison P.T., and Salgia R. Cytokine Growth Factor Rev. 13 (2002) 41
6. Bottaro D.P., Rubin J.S., Faletto D.L., Chan A.M., Kmiecik T.E., VandeWoude G.F., and Aaronson S.A. Science 251 (1991) 802
7. A tabular summary of the role of HGF/SF and Met in various cancers, with links to appropriate references, is available at: http://www.vai.org/met/.
8. Danilkovitch-Miagkova A., and Zbar B. J. Clin. Invest. 109 (2002) 863
9. Cai Z.-W., Wei D., Schroeder G.M., Cornelius L.A.M., Kim K., Chen X.-T., Schmidt R.J., Williams D.K., Tokarski J.S., An Y., Sack J.S., Manne V., Kamath A., Zhang Y., Marathe P., Hunt J.T., Lombardo L.J., Fargnoli J., and Borzilleri R.M. Bioorg. Med. Chem. Lett. 18 (2008) 3224
10. Schroeder G.M., Chen X.-T., Williams D.K., Nirschl D.S., Cai Z.-W., Wei D., Tokarski J.S., An Y., Sack J., Chen Z., Huynh T., Vaccaro W., Poss M., Wautlet B., Gullo-Brown J., Kellar K., Manne V., Hunt J.T., Wong T.W., Lombardo L.J., Fargnoli J., and Borzilleri R.M. Bioorg. Med. Chem. Lett. 18 (2008) 1945
11. Kim K.S., Zhang L., Schmidt R., Cai Z.-W., Wei D., Williams D.K., Lombardo L.J., Trainor G.L., Xie D., Zhang Y., An Y., Sack J.S., Tokarski J.S., Darienzo C., Kamath A., Marathe P., Zhang Y., Lippy J., Jeyaseelan R., Wautlet B., Henley B., Gullo-Brown J., Manne V., Hunt J.T., Fargnoli J., and Borzilleri R.M. J. Med. Chem. 51 (2008) 5330
12. Borzilleri, R. M.; Chen, X.-T.; Williams, D. K.; Tokarski, J. S.; Kaltenbach, R. F. U.S. Patent Application 2007/0078140, 2007.
13. Galeeva R.N., Gavrilov M.Y., Nazmetdinov F.Y., Drovosekova L.P., Kolla V.E., and Kon'shin M.E. Khim. Farm. Zh. 32 (1998) 31
14. Kermack W.O., and Weatherhead A.P. J. Chem. Soc. (1942) 726
15. Yu C., Jiang Y., Liu B., and Hu L. Tetrahedron Lett. 42 (2001) 1449
16. +: calcd: 476.1334, found: 476.1350.
17. +.
18. Christensen J.G., Schreck R., Burrows J., Kuruganti P., Chan E., Le P., Chen J., Wang X., Ruslim L., Blake R., Lipson K.E., Ramphal J., Do S., Cui J.J., Cherrington J.M., and Mendel D.B. Cancer Res. 63 (2003) 7345
19. The atomic coordinates have been deposited in the RCSB Protein Data Bank (PDB code: 3L8V).
20. 50 values of greater than 50 μM.