Design and synthesis of 3-substituted benzamide derivatives as Bcr-Abl kinase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 5, 2006, Pages 1421-1425

  Asaki, Tetsuo ^a   Sugiyama, Yukiteru ^a   Hamamoto, Taisuke ^a   Higashioka, Masaya ^a   Umehara, Masato ^a   Naito, Haruna ^a   Niwa, Tomoko ^a  

^a NIPPON SHINYAKU CO LTD   (Japan)

Author keywords

Bcr Abl; Imatinib; Inhibitor; Structure activity; Tyrosine kinase

Indexed keywords

3 (DIMETHYLAMINO)AZETIDIN 1 YL BENZAMIDE; 3 (DIMETHYLAMINO)PYRROLIDIN 1 YL BENZAMIDE; 3 (DIMETHYLAMINOMETHYL)PYRROLIDIN 1 YL BENZAMIDE; 3 [4,5 DIMETHYLTHIAZOL 2 YL] 2,5 DIPHENYLTETRAZOLIUM BROMIDE; 4 METHYLPIPERAZIN 1 YL BENZAMIDE; BCR ABL PROTEIN; BENZAMIDE DERIVATIVE; IMATINIB; NS 187; PROTEIN TYROSINE KINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CHRONIC MYELOID LEUKEMIA; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA CELL LINE; STRUCTURE ACTIVITY RELATION;

BENZAMIDES; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG DESIGN; FUSION PROTEINS, BCR-ABL; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN KINASE INHIBITORS; PROTEIN STRUCTURE, TERTIARY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 31344435118     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.11.042     Document Type: Article

References (25)

1. M.W.N. Deininger, J.M. Goldman, and J.V. Melo Blood 96 2000 3343
2. B.J. Druker, S. Tamura, E. Buchdunger, S. Ohno, G.M. Segal, S. Fanning, J. Zimmermann, and N.B. Lydon Nat. Med. 2 1996 561
3. B.J. Druker, C.L. Sawyers, H. Kantarjian, D.J. Resta, S.F. Reese, J.M. Ford, R. Capdeville, and M. Talpaz N. Engl. J. Med. 344 2001 1038
4. K. Peggs, and S. Mackinnon N. Engl. J. Med. 348 2003 1048
5. M. Kalaycio Curr. Hematol. Rep. 3 2004 37
6. T. Schindler, W. Bornmann, P. Pellicena, W.T. Miller, B. Clarkson, and J. Kuriyan Science 289 2000 1938
7. B. Nagar, W.G. Bornmann, P. Pellicena, T. Schindler, D.R. Veach, W.T. Miller, B. Clarkson, and J. Kuriyan Cancer Res. 62 2002 4236
8. N.P. Shah, and C.L. Sawyers Oncogene 22 2003 7389
9. A.J. Tipping, F.X. Mahon, V. Lagarde, J.M. Goldman, and J.V. Melo Blood 98 2001 3864
10. F.X. Mahon, M.W.N. Deininger, B. Schultheis, J. Chabrol, J. Reiffers, J.M. Goldman, and J.V. Melo Blood 96 2000 1070
11. E. Weisberg, and J.D. Griffin Blood 95 2000 3498
12. P. le Coutre, E. Tassi, M. Varella-Garcia, R. Barni, L. Mologni, G. Cabrita, E. Marchesi, R. Supino, and C. Cambarcorti-Passerini Blood 95 2000 1758
13. M.E. Gorre, M. Mohammed, K. Ellwood, N. Hsu, R. Paquette, P.N. Rao, and C.L. Sawyers Science 293 2001 876
14. A. Hochhaus, S. Kreil, A. Corbin, P. La Rosee, T. Lahaye, U. Berger, N.C.P. Cross, W. Linkesch, B.J. Druker, and R. Hehlmann Science 293 2001 2163
15. C. Barthe, P. Cony-Makhoul, J.V. Melo, J. Reiffers, and F.X. Mahon Science 293 2001 2163
16. S. Branford, Z. Rudzki, S. Walsh, A. Grigg, C. Arthur, K. Taylor, R. Herrmann, K.P. Lynch, and T.P. Hughes Blood 99 2002 3472
17. J. Zimmermann, E. Buchdunger, H. Mett, T. Meyer, N.B. Lydon, and P. Traxler Bioorg. Med. Chem. Lett. 6 1996 1221
18. D. Kikuchi, S. Sakaguchi, and Y. Ishii J. Org. Chem. 63 1998 6023
19. T. Mosmann J. Immunol. Methods 65 1983 55
20. S. Kimura, H. Naito, H. Segawa, J. Kuroda, T. Yuasa, K. Sato, A. Yokota, Y. Kamitsuji, E. Kawata, E. Ashihara, Y. Nakaya, H. Naruoka, T. Wakayama, K. Nasu, T. Asaki, T. Niwa, K. Hirabayashi, and T. Maekawa Blood 106 2005 3948
21. C. Hansch, and A. Leo Exploring QSAR: Fundamentals and Applications in Chemistry and Biology 1995 American Chemical Society Washington, DC
22. Q. Li, D.T.W. Chu, A. Claiborne, C.S. Cooper, C.M. Lee, K. Raye, K.B. Berst, P. Donner, W. Wang, L. Hasvold, A. Fung, Z. Ma, M. Tufano, R. Flamm, L.L. Shen, J. Baranowski, A. Nilius, J. Alder, J. Meulbroek, K. Marsh, D. Crowell, Y. Hui, L. Seif, L.M. Melcher, R. Henry, S. Spanton, R. Faghih, L.L. Klein, S.K. Tanaka, and J.J. Plattner J. Med. Chem. 39 1996 3070
23. T.A. Halgren J. Comput. Chem. 17 1996 490
24. N.J. Donato, J.Y. Wu, J. Stapley, G. Gallick, H. Lin, R. Arlinghaus, and M. Talpaz Blood 101 2003 690
25. A. Ptasznik, Y. Nakata, A. Kalota, S.G. Emerson, and A.M. Gewirtz Nat. Med. 10 2004 1187