Synthesis of novel diarylamino-1,3,5-triazine derivatives as FAK inhibitors with anti-angiogenic activity

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 16, 2013, Pages 4552-4556

  Dao, Pascal ^a   Jarray, Rafika ^a   Le Coq, Johanne ^b   Lietha, Daniel ^b   Loukaci, Ali ^a   Lepelletier, Yves ^c   Hadj Slimane, Réda ^d   Garbay, Christiane ^a   Raynaud, Françoise ^a   Chen, Huixiong ^a,e  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b Centro Nacional de Investigaciones Oncológicas   (Spain)

^c CNRS   (France)

^d Visiotact Pharma   (France)

^e GUANGDONG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Anti angiogenic activity; Diarylamino 1,3,5 triazines; FAK inhibitors; Synthesis; X ray structure

Indexed keywords

2 [5 CHLORO 2 (2 METHOXY 4 MORPHOLINOANILINO) 4 PYRIMIDINYLAMINO] N METHYLBENZAMIDE; ANGIOGENESIS INHIBITOR; FOCAL ADHESION KINASE INHIBITOR; GUANIDINE DERIVATIVE; TRIAZINE DERIVATIVE;

ANTIANGIOGENIC ACTIVITY; ARTICLE; BINDING AFFINITY; CELL VIABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME BINDING; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; MICROWAVE RADIATION; PROTEIN DOMAIN; STRUCTURE ACTIVITY RELATION; UMBILICAL VEIN ENDOTHELIAL CELL; X RAY CRYSTALLOGRAPHY;

ANTI-ANGIOGENIC ACTIVITY; DIARYLAMINO-1,3,5-TRIAZINES; FAK INHIBITORS; SYNTHESIS; X-RAY STRUCTURE;

ANGIOGENESIS INHIBITORS; CELL SURVIVAL; CRYSTALLOGRAPHY, X-RAY; ENDOTHELIAL CELLS; ENZYME ACTIVATION; ENZYME INHIBITORS; FOCAL ADHESION PROTEIN-TYROSINE KINASES; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; MOLECULAR STRUCTURE; MORPHOLINES; TRIAZINES;

EID: 84880626555     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2013.06.038     Document Type: Article

References (27)

1. P. Carmeliet Nat. Med. 9 2003 653
2. A. Veeravagu, A.R. Hsu, W. Cai, L.C. Hou, V.C. Tse, and X. Chen Recent Pat. Anticancer Drug Discovery 2 2007 59
3. R.S. Kerbel Cancer Metastasis Rev. 20 2001 1
4. T.L. Shen, A.Y. Park, A. Alcaraz, X. Peng, I. Jang, P. Koni, R.A. Flavell, H. Gu, and J.L.J. Guan Cell Biol. 169 2005 941
5. R. Braren, H. Hu, Y.H. Kim, H.E. Beggs, L.F. Reichardt, and R.J. Wang Cell Biol. 172 2006 151
6. B. Tavora, S. Batista, L.E. Reynolds, S. Jadeja, S. Robinson, V. Kostourou, I. Hart, M. Fruttiger, M. Parsons, and K.M. Hodivala-Dilke EMBO Mol. Med. 2 2010 516
7. V. Gabarra-Niecko, M.D. Schaller, and J.M. Dunty Cancer Metastasis Rev. 22 2003 359
8. J. Halder, Y.G. Lin, W.M. Merritt, W.A. Spannuth, A.M. Nick, T. Honda, A.A. Kamat, L.Y. Han, T.J. Kim, C. Lu, A.M. Tari, W. Bornmann, A. Fernandez, G. Lopez-Berestein, and A.K. Sood Cancer Res. 67 2007 10976
9. L. Gillory, and E.A. Beierle Anticancer Agents Med. Chem. 10 2010 714
10. G.A. Infusino, and J.R. Jacobson Microvasc. Res. 83 2012 89
11. M. Negwer Organic-Chemical Drugs and their Synonyms 2001 Wiley-VCH Verlag GmbH Weinheim
12. Kondoh, Y.; Iikubo, K.; Kuromitsu, S.; Shindo, N.; Soga, T.; Furutani, T.; Shimada, I.; Matsuya, T.; Kurosawa, K.; Kamikawa, A.; Mano, H.; International Patent WO/2009/008371, 2009.
13. R.T. Bossi, M.B. Saccardo, E. Ardini, M. Menichincheri, L. Rusconi, P. Magnaghi, P. Orsini, N. Avanzi, A.L. Borgia, M. Nesi, T. Bandiera, G. Fogliatto, and J.A. Bertrand Biochemistry 49 2010 6813
14. S. Nozaki, M. Maeda, H. Tsuda, and G.W. Sledge Jr. Breast Cancer Res. Treat. 83 2004 195
15. H. Chen, P. Dao, A. Laporte, and C. Garbay Tetrahedron Lett. 51 2010 3174
16. P. Dao, C. Garbay, and H. Chen Tetrahedron 68 2012 3856
17. T.J. Liu, T. LaFortune, T. Honda, O. Ohmori, S. Hatakeyama, T. Meyer, D. Jackson, J. de Groot, and W.K. Yung Mol. Cancer Ther. 6 2007 1357
18. Garcia-Echeverria, C.; Kanazawa, T.; Kawahara, E.; Masuya, K.; Matsuura, N.; Miyake, T.; Ohmori, O.; Umemura, I.; Steensma, R.; Chopiuk, G.; Jiang, J.; Wan, Y.; Ding, Q.; Zhang, Q.; Gray, N. S.; Karanewsky, D. International Patent WO 2005/016894 A1, 2005.
19. S.E.J. Hughes Histochem. Cytochem. 45 1997 1005
20. M. Presta, P. Dell'Era, S. Mitola, E. Moroni, R. Ronca, and M. Rusnati Cytokine Growth Factor Rev. 16 2005 159
21. W. Kabsch Acta Crystallogr. 66 2010 125
22. A.J. McCoy, R.W. Grosse-Kunstleve, P.D. Adams, M.D. Winn, L.C. Storoni, and R.J.J. Read Appl. Crystallogr. 40 2007 658
23. G.N. Murshudov, A.A. Vagin, and E.J. Dodson Acta Crystallogr. D Biol. Crystallogr. 53 1997 240
24. P. Emsley, and K. Cowtan Acta Crystallogr. D Biol. Crystallogr. 60 2004 2126
25. A.W. Schüttelkopf, and D.M. van Aalten Acta Crystallogr. D Biol. Crystallogr. 60 2004 1355
26. D. Lietha, and M.J. Eck PLoS One 3 2008 e3800
27. Y. Kawasaki, E.E. Chufan, V. Lafont, K. Hidaka, Y. Kiso, L. Mario-Amzel, and E. Freire Chem. Biol. Drug Des. 75 2010 143