Development of isoform selective PI3-kinase inhibitors as pharmacological tools for elucidating the PI3K pathway

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 17, 2012, Pages 5445-5450

  Bruce, Ian ^a   Akhlaq, Mohammed ^a   Bloomfield, Graham C ^a   Budd, Emma ^a   Cox, Brian ^a   Cuenoud, Bernard ^a   Finan, Peter ^a   Gedeck, Peter ^a   Hatto, Julia ^a   Hayler, Judy F ^a   Head, Denise ^a   Keller, Thomas ^a   Kirman, Louise ^a   Leblanc, Catherine ^a   Grand, Darren Le ^a   McCarthy, Clive ^a   O'Connor, Desmond ^a   Owen, Charles ^a   Oza, Mrinalini S ^a   Pilgrim, Gaynor ^a   Press, Nicola E ^a   Sviridenko, Lilya ^a   Whitehead, Lewis ^a   more..

^a NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

Aminothiazoles; Isoform selectivity; Parallel synthesis; Pharmacological tools; PI3 Kinase inhibitors

Indexed keywords

5 (6 QUINOXALINYLMETHYLENE) 2,4 THIAZOLIDINEDIONE; 5 FLUORO 3 PHENYL 2 [1 (9H PURIN 6 YLAMINO)PROPYL] 3H QUINAZOLIN 4 ONE; 9 (1 ANILINOETHYL) 7 METHYL 2 MORPHOLINOPYRIDO[1,2 A]PYRIMIDIN 4 ONE; DNA; MAMMALIAN TARGET OF RAPAMYCIN; PHOSPHATIDYLINOSITOL 3 KINASE; PHOSPHATIDYLINOSITOL 3 KINASE INHIBITOR; PIK 90; PROTEIN KINASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CELL ACTIVITY; SYNTHESIS;

ANIMALS; CATALYTIC DOMAIN; FEMALE; HUMANS; MICE; MODELS, MOLECULAR; PHOSPHATIDYLINOSITOL 3-KINASES; PROTEIN ISOFORMS; PROTEIN KINASE INHIBITORS; RATS; SIGNAL TRANSDUCTION; THIAZOLES;

EID: 84865126288     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.07.042     Document Type: Article

References (30)

1. B. Vanhaesebroeck, S. Leevers, K. Ahmadi, J. Timms, R. Katso, P.C. Driscoll, R. Woscholski, P.J. Parker, and M.D. Waterfield Annu. Rev. Biochem. 70 2001 535
2. M. Wymann, and L. Pirola Biochim. Biophys. Acta 1436 1998 127
3. R.T. Abraham DNA Repair 3 2004 883
4. R.C. Stein, and M.D. Waterfield Mol. Med. Today 6 2000 347
5. S. Ward, Y. Sotsios, J. Dowden, I. Bruce, and P. Finan Chem. Biol. 10 2003 207
6. M. Thomas, and C. Owen Cur. Opin. Pharmacol. 8 2008 267
7. R. Marone, V. Cmiljanovic, B. Giese, and M.P. Wymann Biochim. Biophys. Acta Proteins Proteomics 1784 2008 159
8. S.J. Shuttleworth, F.A. Silva, A.R.L. Cecil, C.D. Tomassi, T.J. Hill, F.I. Raynaud, P.A. Clarke, and P. Workman Curr. Med. Chem. 18 2011 2687
9. Shimada, M.; Murata, T.; Fuchikami, K.; Tsujishita, H.; Omori, N.; Kato, I.; Miura, M.; Urbahns, K.; Gantner, F.; Bacon, K. WO 2004029055, 2004. See also reference 18 which describes structural studies with PIK-90.
10. J.J. Hollick, L.J.M. Rigoreau, C. Cano-Soumillac, X. Cockcroft, N.J. Curtin, M. Frigerio, B.T. Golding, S. Guiard, I.R. Hardcastle, I. Hickson, M.G. Hummersone, K.A. Menear, N.M.B. Martin, I. Matthews, D.R. Newell, R. Ord, C.J. Richardson, G.C.M. Smith, and R.J. Griffin J. Med. Chem. 2007 1958 50
11. M. Camps, T. Ruckle, H. Ji, V. Ardissone, F. Rintelen, J. Shaw, C. Ferrandi, C. Chabert, C. Gillieron, B. Francon, T. Martin, D. Gretener, D. Perrin, D. Leroy, P.A. Vitte, E. Hirsch, M.P. Wymann, R. Cirillo, M.K. Schwartz, and C. Rommel Nat. Med. 11 2005 936
12. Robertson, A. D.; Jackson, S.; Kenche, A.; Yaip, C.; Parbaharan, H.; Thompson, P. WO 200153266, 2001.
13. S.E. Herman, A.L. Gordon, A.J. Wagner, N.A. Heerema, W. Zhao, J.M. Flynn, J. Jones, L. Andritsos, K.D. Puri, B.J. Lannutti, N.A. Giese, X. Zhang, L. Wei, J.C. Byrd, and A.J. Johnson Blood. 116 2010 2078
14. R. Chaisuparat, J. Hu, B.C. Jham, Z.A. Knight, K.M. Shokat, and S. Montaner Cancer Res. 68 2008 8361
15. (b) C. Rommel Curr. Top. Microbiol. Immunol. 1 2010 279
16. A.M. Condliffe, K. Davidson, K.E. Anderson, C.D. Ellson, T. Crabbe, K. Okkenhaug, B. Vanhaesebroeck, M. Turner, L. Webb, M.P. Wymann, E. Hirsch, T. Ruckle, M. Camps, C. Rommel, S.P. Jackson, E.R. Chilvers, L.R. Stephens, and P.T. Hawkins Blood 106 2005 1432
17. M.H. Julius, C.H. Heusser, and K.H. Hartmann Eur. J. Immunol 14 1984 753
18. E.H. Walker, O. Perisic, C. Reid, L. Stephens, and R.L. Williams Nature 402 1999 313
19. Z.A. Knight, B. Gonzalez, M.E. Feldman, E.R. Zunder, D.D. Goldenberg, O. Williams, R. Loewith, D. Stokoe, A. Balla, B. Toth, T. Balla, W.A. Weiss, R.L. Williams, and K.M. Shokat Cell 125 2006 733
20. Z.A. Knight, G.G. Chiang, P.J. Alaimo, D.M. Kenski, C.B. Ho, K. Coan, R.T. Abraham, and K.M. Shokat Bioorg. Med. Chem. 12 2004 4749
21. A. Ulman, and E. Urankar J. Org. Chem. 54 1989 4691
22. T. Sargent III, A.T. Shulgin, and C.A. Mathis J. Med. Chem. 1071 1984 27
23. L.C. King, and R.J. Hlavacek J. Am. Chem. Soc. 72 1950 3722
24. Ni, Z-J.; Pecchi, S.; Burger, M.; Han, W.; Smith, A.; Atallah, G.; Bartulis, S.; Frazier, K.; Verhagen, J.; Zhang, Y.; Iwanowicz, E.; Hendrickson, T.; Knapp, M.; Merritt, H.; Voliva, C.; Wiesmann, M.; Le Grand, D. M.; Bruce, I.; Dale, J.; Lan, J.; Levine, B.; Costales, A.; Liu, J.; Pick, T.; Menezes, D. WO 2007095588, 2007.
25. R. H. Fairhurst, R. H.; P. Imbach, P. WO 2009080705, 2009.
26. S. Jamieson, J.U. Flanagan, S. Kolekar, C. Buchanan, J.D. Kendall, W.J. Lee, G.W. Rewcastle, W.A. Denny, R. Singh, J. Dickson, B.C. Baguley, and P.R. Shepherd Biochem. J. 438 2011 53
27. Z. Zheng, S.I. Amran, J. Zhu, O. Schmidt-Kittler, K.W. Kinzler, B. Vogelstein, P.R. Shepherd, P.E. Thompson, and I. Jennings Biochem. J. 444 2012 529
28. Bruce, I.; Weitz, G.S. WO 2008000421, 2008.
29. Budd, E.; Hatto, J. D. I.; Hayler, J. F.; Le Grand, D. M.; Valade, B. WO 2007068473, 2007.
30. Bloomfield, G. C.; Bruce, I.; Hayler, J. F.; Leblanc, C.; Le Grand, D. M.; McCarthy, C. WO 2005021519, 2005.