Regioselective synthesis of 5- and 6-methoxybenzimidazole-1,3,5-triazines as inhibitors of phosphoinositide 3-kinase

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 3, 2013, Pages 802-805

  Miller, Michelle S ^a   Pinson, Jo Anne ^a   Zheng, Zhaohua ^a   Jennings, Ian G ^a   Thompson, Philip E ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

Benzimidazole derivatives; Phosphoinositide 3 kinase inhibitors; Regioselective synthesis; ZSTK474

Indexed keywords

2 (2 DIFLUOROMETHYLBENZIMIDAZOL 1 YL) 4,6 DIMORPHOLINO 1,3,5 TRIAZINE; 4,4' [6 (5 METHOXY 2 DIFLUOROMETHYL 1H BENZO[DEXTRO]IMIDAZOL 1 YL) 1,3,5-TRIAZINE-2,4-DIYL]DIMORPHOLINE; 5 METHOXYBENZIMIDAZOLE 1,3,5 TRIAZINE DERIVATIVE; 6 METHOXYBENZIMIDAZOLE 1,3,5 TRIAZINE DERIVATIVE; ANTINEOPLASTIC AGENT; PHOSPHATIDYLINOSITOL 3 KINASE; PHOSPHATIDYLINOSITOL 3 KINASE INHIBITOR; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG POTENCY; DRUG SYNTHESIS; IC 50; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANILINE COMPOUNDS; BENZIMIDAZOLES; ENZYME ACTIVATION; ENZYME INHIBITORS; NITRO COMPOUNDS; PHOSPHATIDYLINOSITOL 3-KINASES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZINES;

EID: 84872349849     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.11.076     Document Type: Article

References (25)

1. B. Vanhaesebroeck, J. Guillermet-Guibert, M. Graupera, and B. Bilanges Nat. Rev. Mol. Cell Biol. 11 2010 329
2. J.A. Engelman Nat. Rev. Cancer 9 2009 550
3. P. Liu, H. Cheng, T.M. Roberts, and J.J. Zhao Nat. Rev. Drug Disc. 8 2009 627
4. S. Yaguchi, Y. Fukui, I. Koshimizu, H. Yoshimi, T. Matsuno, H. Gouda, S. Hirono, K. Yamazaki, and T. Yamori J. Natl. Cancer Inst. 98 2006 545
5. Sugama, T.; Ishihara, N.; Tanaka, Y.; Takahashi, M.; Yaguchi, S.; Watanabe, T. WO2009066775, 2009.
6. A. Berndt, S. Miller, O. Williams, D.D. Le, B.T. Houseman, J.I. Pacold, F. Gorrec, W.-C. Hon, Y. Liu, C. Rommel, P. Gaillard, T. Rückle, M.K. Schwarz, K.M. Shokat, J.P. Shaw, and R.L. Williams Nat. Chem. Biol. 6 2010 117
7. G.W. Rewcastle, S.A. Gamage, J.U. Flanagan, R. Frederick, W.A. Denny, B.C. Baguley, P. Kestell, R. Singh, J.D. Kendall, E.S. Marshall, C.L. Lill, W.-J. Lee, S. Kolekar, C.M. Buchanan, S.M.F. Jamieson, and P.R. Shepherd J. Med. Chem. 54 2011 7105
8. M.A. Clark, R.A. Acharya, C.C. Arico-Muendel, S.L. Belyanskaya, D.R. Benjamin, N.R. Carlson, P.A. Centrella, C.H. Chiu, S.P. Creaser, J.W. Cuozzo, C.P. Davie, Y. Ding, G.J. Franklin, K.D. Franzen, M.L. Gefter, S.P. Hale, N.J.V. Hansen, D.I. Israel, J. Jiang, M.J. Kavarana, M.S. Kelley, C.S. Kollmann, F. Li, K. Lind, S. Mataruse, P.F. Medeiros, J.A. Messer, P. Myers, H. O'Keefe, M.C. Oliff, C.E. Rise, A.L. Satz, S.R. Skinner, J.L. Svendsen, L. Tang, K. van Vloten, R.W. Wagner, G. Yao, B. Zhao, and B.A. Morgan Nat. Chem. Biol. 5 2009 647
9. Andrews, I.; Cheung, M.; Davis-Ward, R.; Drewry, D.; Emmitte, K.; Hubbard, R.; Kuntz, K.; Linn, J.; Mook, R.; Smith, G.; Veal, J. WO2004014899, 2004.
10. Armstrong, H.; Beresis, R.; Goulet, J.; Holmes, M.; Hong, X.; Mills, S.; Parsons, W.; Sinclair, P.; Steiner, M.; Wong, F.; Zaller, D. WO0100213, 2001.
11. L.C.R. Carvalho, E. Fernandes, and M.M.B. Marques Chem. Eur. J. 17 2011 12544
12. H.-F. He, Z.-J. Wang, and W. Bao Adv. Synth. Catal. 352 2010 2905
13. C.T. Brain, and S.A. Brunton Tetrahedron Lett. 43 2002 1893
14. G. Brasche, and S.L. Buchwald Angew. Chem. 120 2008 1958
15. P. Saha, T. Ramana, N. Purkait, M.A. Ali, R. Paul, and T. Punniyamurthy J. Org. Chem. 74 2009 8719
16. J. Peng, M. Ye, C. Zong, F. Hu, L. Feng, X. Wang, Y. Wang, and C. Chen J. Org. Chem. 76 2010 716
17. N. Zheng, and S.L. Buchwald Org. Lett. 9 2007 4749
18. N. Zheng, K.W. Anderson, X. Huang, H.N. Nguyen, and S.L. Buchwald Angew. Chem., Int. Ed. 46 2007 7509
19. B. Zou, Q. Yuan, and D. Ma Angew. Chem., Int. Ed. 46 2007 2598
20. K.R. Hornberger, J.G. Badiang, J.M. Salovich, K.W. Kuntz, K.A. Emmitte, and M. Cheung Tetrahedron Lett. 49 2008 6348
21. R.T. Skerlj, C.M. Bastos, M.L. Booker, M.L. Kramer, R.H. Barker, C.A. Celatka, T.J. O'Shea, B. Munoz, A.B. Sidhu, J.F. Cortese, S. Wittlin, P. Papastogiannidis, I. Angulo-Barturen, M.B. Jimenez-Diaz, and E. Sybertz ACS Med. Chem. Lett. 2 2011 708
22. D.J. Davies, M. Crowe, N. Lucas, J. Quinn, D.D. Miller, S. Pritchard, D. Grose, E. Bettini, N. Calcinaghi, C. Virginio, L. Abberley, P. Goldsmith, A.D. Michel, I.P. Chessell, J.N.C. Kew, N.D. Miller, and M.J. Gunthorpe Bioorg. Med. Chem. Lett. 22 2012 2620
23. F.D. Bellamy, and K. Ou Tetrahedron Lett. 25 1984 839
24. G. Navarrete-Vázquez, S. Hidalgo-Figueroa, M. Torres-Piedra, J. Vergara-Galicia, J.C. Rivera-Leyva, S. Estrada-Soto, I. León-Rivera, B. Aguilar-Guardarrama, Y. Rios-Gómez, R. Villalobos-Molina, and M. Ibarra-Barajas Bioorg. Med. Chem. 18 2010 3985
25. M.S. Kabir, O.A. Namjoshi, R. Verma, R. Polanowski, S.M. Krueger, D. Sherman, M.A. Rott, W.R. Schwan, A. Monte, and J.M. Cook Bioorg. Med. Chem. 18 2010 4178