Inhibitors of the TAM subfamily of tyrosine kinases: Synthesis and biological evaluation

European Journal of Medicinal Chemistry

Volumn 61, Issue , 2013, Pages 2-25

  Suárez, Rosa M ^a   Chevot, Franciane ^a   Cavagnino, Andrea ^b,c   Saettel, Nicolas ^a   Radvanyi, François ^a   Piguel, Sandrine ^a,d   Bernard Pierrot, Isabelle ^a   Stoven, Véronique ^b,c   Legraverend, Michel ^a  

^a CNRS   (France)

^b PSL RESEARCH UNIVERSITY   (France)

^c INSERM U900   (France)

^d UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

Docking; Molecular modelling; TAM subfamily; Tyrosine kinase inhibitors

Indexed keywords

ANTINEOPLASTIC AGENT; BMS 777607; MERR PROTEIN; N [4 (9H PURIN 6 YLAMINO) 3 FLUOROPHENYL] 1 (3 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [4 (9H PURIN 6 YLAMINO) 3 FLUOROPHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [4 (9H PURIN 6 YLAMINO) 3 FLUOROPHENYL] 2 OXO 1 [4 (TRIFLUOROMETHYL)PHENYL] 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [4 (9H PURIN 6 YLAMINO) 3 FLUOROPHENYL] 2 OXO- 1 [3 (TRIFLUOROMETHYL)PHENYL] 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [4 (9H PURIN 6 YLAMINO)PHENYL] 1 (3 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [4 (9H PURIN 6 YLOXY) 3 FLUOROPHENYL] 1 (3 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [4 (9H PURIN 6 YLOXY) 3 FLUOROPHENYL] 1 (4 FLUOROPHENYL) 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [4 (9H PURIN 6 YLOXY) 3 FLUOROPHENYL] 2 OXO 1 [4 (TRIFLUOROMETHYL)PHENYL] 1,2 DIHYDROPYRIDINE 3 CARBOXAMIDE; N [4 (9H PURIN 6 YLOXY) 3-FLUOROPHENYL]2 FLUOROBENZAMIDE; PROTEIN AXL; PROTEIN TYRO 3; PROTEIN TYROSINE KINASE; PROTEIN TYROSINE KINASE INHIBITOR; SUNITINIB; TRANSCRIPTION FACTOR; UNCLASSIFIED DRUG; VANDETANIB;

ALLOSTERISM; AMINO ACID SEQUENCE; ARTICLE; CONTROLLED STUDY; EVALUATION; HINGE REGION; HUMAN; MOLECULAR DOCKING; PROTEIN INTERACTION; PROTEIN STRUCTURE; SYNTHESIS;

ANIMALS; CELLS, CULTURED; CERCOPITHECUS AETHIOPS; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN KINASE INHIBITORS; RECEPTOR PROTEIN-TYROSINE KINASES; STRUCTURE-ACTIVITY RELATIONSHIP; VERO CELLS;

EID: 84874937924     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.06.005     Document Type: Article

References (44)

1. D.R. Robinson, Y.-M. Wu, and S.-F. Lin Oncogene 19 2000 5548 5557
2. R.M.A. Linger, A.K. Keating, H.S. Earp, and D.K. Graham Adv. Canc. Res. 2008 35 83
3. D.K. Graham, T.L. Dawson, D.L. Mullaney, H.R. Snodgrass, and H.S. Earp Cell Growth Differ. 5 1994 647 657
4. R.M. Linger, A.K. Keating, H.S. Earp, and D.K. Graham Expert Opin. Ther. Targets 14 2010 1073 1090
5. S. Zhu, H. Wurdak, Y. Wang, A. Galkin, H. Tao, J. Li, C.A. Lyssiotis, F. Yan, B.P. Tu, L. Miraglia, J. Walker, F. Sun, A. Orth, P.G. Schultz, and X. Wu Proc. Natl. Acad. Sci. U.S.A. 106 2009 17025 17030
6. Y. Liu, and N.S. Gray Nat. Chem. Biol. 2 2006 358 364
7. H.G. Choi, P. Ren, F.J. Adrian, F. Sun, H.S. Lee, X. Wang, Q. Ding, G. Zhang, Y. Xie, J. Zhang, Y. Liu, T. Tuntland, M. Warmuth, P.W. Manley, J. Mestan, N.S. Gray, and T. Sim J. Med. Chem. 53 2010 5439 5448
8. B. Okram, A. Nagle, F.J. Adri·n, C. Lee, P. Ren, X. Wang, T. Sim, Y. Xie, X. Wang, G. Xia, G. Spraggon, M. Warmuth, Y. Liu, and N.S. Gray Chem. Biol. 13 2006 779 786
9. W.L. Delano, DeLano Scientific LLC, San Carlos, CA, USA. http://www.pymol.org.
10. T. Zhou, L. Commodore, W.-S. Huang, Y. Wang, T.K. Sawyer, W.C. Shakespeare, T. Clackson, X. Zhu, and D.C. Dalgarno Chem. Biol. Drug Design 75 2010 18 28
11. P. Bhargava, and M.O. Robinson Curr. Oncol. Rep. 13 2011 103 111
12. A. Mollard, S.L. Warner, L.T. Call, M.L. Wade, J.J. Bearss, A. Verma, S. Sharma, H. Vankayalapati, and D.J. Bearss ACS Med. Chem. Lett. 2 2011 907 912
13. J.M.L. Ebos, C.R. Lee, W. Cruz-Munoz, G.A. Bjarnason, J.G. Christensen, and R.S. Kerbel Cancer Cell 15 2009 232 239
14. M.W. Karaman, S. Herrgard, D.K. Treiber, P. Gallant, C.E. Atteridge, B.T. Campbell, K.W. Chan, P. Ciceri, M.I. Davis, P.T. Edeen, R. Faraoni, M. Floyd, J.P. Hunt, D.J. Lockhart, Z.V. Milanov, M.J. Morrison, G. Pallares, H.K. Patel, S. Pritchard, L.M. Wodicka, and P.P. Zarrinkar Nat. Biotechnol. 26 2008 127 132
15. X. Huang, P. Finerty Jr., J.R. Walker, C. Butler-Cole, M. Vedadi, M. Schapira, S.A. Parker, B.E. Turk, D.A. Thompson, and S. Dhe-Paganon J. Struct. Biol. 165 2009 88 96
16. A. Ullrich, P. Knyazev, Y. Zhang, K. György, L. Örfi, I. Szabadkai, in: WO 2009/127417 A1, DE, 2009, pp. 1-201.
17. N.A. Powell, J.T. Kohrt, K.J. Filipski, M. Kaufman, D. Sheehan, J.E. Edmunds, A. Delaney, Y. Wang, F. Bourbonais, D.-Y. Lee, F. Schwende, F. Sun, P. McConnell, C. Catana, H. Chen, J. Ohren, and L.A. Perrin Bioorg. Med. Chem. Lett. 22 2012 190 193
18. G.M. Schroeder, Y. An, Z.-W. Cai, X.-T. Chen, C. Clark, L.A.M. Cornelius, J. Dai, J. Gullo-Brown, A. Gupta, B. Henley, J.T. Hunt, R. Jeyaseelan, A. Kamath, K. Kim, J. Lippy, L.J. Lombardo, V. Manne, S. Oppenheimer, J.S. Sack, R.J. Schmidt, G. Shen, K. Stefanski, J.S. Tokarski, G.L. Trainor, B.S. Wautlet, D. Wei, D.K. Williams, Y. Zhang, Y. Zhang, J. Fargnoli, and R.M. Borzilleri J. Med. Chem. 52 2009 1251 1254
19. J. Porter Expert Opin. Ther. Patents 20 2010 159 177
20. D.K. Williams, X.-T. Chen, C. Tarby, R. Kaltenbach, Z.-W. Cai, J.S. Tokarski, Y. An, J.S. Sack, B. Wautlet, J. Gullo-Brown, B.J. Henley, R. Jeyaseelan, K. Kellar, V. Manne, G.L. Trainor, L.J. Lombardo, J. Fargnoli, and R.M. Borzilleri Bioorg. Med. Chem. Lett. 20 2010 2998 3002
21. X. Lv, and W. Bao J. Org. Chem. 72 2007 3863 3867
22. N. Ibrahim, F. Chevot, and M. Legraverend Tet. Lett. 52 2011 305 307
23. M.J. Robins, E.F. Godefroi, T. E.C., L.R. Lewis, and A. Jackson J. Am. Chem. Soc. 83 1961 2574 2579
24. B.P. Fors, P. Krattiger, E. Strieter, and S.L. Buchwald Org. Lett. 10 2008 3505 3508
25. P. Capek, M. Vrábel, Z. Hasník, R. Pohl, and M. Hocek Synthesis 2006 3515 3526
26. T. Borrmann, A. Abdelrahman, R. Volpini, C. Lambertucci, E. Alksnis, S. Gorzalka, M. Knospe, A.C. Schiedel, G. Cristalli, and C.E. Müller J. Med. Chem. 52 2009 5974 5989
27. M.A. Fabian, W.H. Biggs, D.K. Treiber, C.E. Atteridge, M.D. Azimioara, M.G. Benedetti, T.A. Carter, P. Ciceri, P.T. Edeen, M. Floyd, J.M. Ford, M. Galvin, J.L. Gerlach, R.M. Grotzfeld, S. Herrgard, D.E. Insko, M.A. Insko, A.G. Lai, J.-M. Lélias, S.A. Mehta, Z.V. Milanov, A.M. Velasco, L.M. Wodicka, H.K. Patel, P.P. Zarrinkar, and D.J. Lockhart Nat. Biotechnol. 23 2005 329 336
28. K. Stierand, and M. Rarey ChemMedChem 2 2007 853 860
29. M.R. McGann, H.R. Almond, A. Nicholls, J.A. Grant, and F.K. Brown Biopolymers 68 2003 76 90
30. L.M. Wodicka, P. Ciceri, M.I. Davis, J.P. Hunt, M. Floyd, S. Salerno, X.H. Hua, J.M. Ford, R.C. Armstrong, P.P. Zarrinkar, and D.K. Treiber Chem. Biol. 17 2010 1241 1249
31. D. Mucs, R.A. Bryce, and P. Bonnet J. Comput. Aided Mol. Des. 25 2011 569 581
32. JJ.-L. Liao J. Med. Chem. 50 2007 409 424
33. F. Milletti, and J.C. Hermann ACS Med. Chem. Lett. 3 2012 383 386
34. L. Vandromme, M. Legraverend, S. Kreimerman, O. Lozach, L. Meijer, and D.S. Grierson Bioorg. Med. Chem. 15 2007 130 141
35. A. Fiser, and A. Sali J.A.R.M.S. Charles, W. Carter, Macromolecular Crystallography, Part D vol. 374 2003 Academic Press 461 491
36. S.F. Altschul, W. Gish, W. Miller, E.W. Myers, and D.J. Lipman J. Mol. Biol. 215 1990 403 410
37. S.R. Eddy Nat. Biotechnol. 22 2004 1035 1036
38. F. Armougom, S.B. Moretti, O. Poirot, S.P. Audic, P. Dumas, B. Schaeli, V. Keduas, and C. Notredame Nucleic Acids Res. 34 2006 W604 W608
39. C.D. Notredame, D.G. Higgins, and J. Heringa J. Mol. Biol. 302 2000 205 217
40. P. Benkert, M. Künzli, and T. Schwede Nucleic Acids Res. 37 2009 W510 W514
41. I.W. Davis, A. Leaver-Fay, V.B. Chen, J.N. Block, G.J. Kapral, X. Wang, L.W. Murray, W.B. Arendall, J. Snoeyink, J.S. Richardson, and D.C. Richardson Nucleic Acids Res. 35 2007 W375 W383
42. M. McGann, and J. Chem Inf. Model. 51 2011 578 596
43. OEChem, Version 1.7.4 2010 OpenEye Scientific Software, Inc. Santa Fe, NM, USA
44. Y. Cheng, and W.H. Prusoff Biochem. Pharmacol. 22 1973 3099 3108