Design and chemical synthesis of [1,2,4]triazol[1,5-c]pyrimidin-5-yl amines, a novel class of VEGFR-2 kinase inhibitors

Tetrahedron Letters

Volumn 50, Issue 27, 2009, Pages 3809-3812

  Kiselyov, Alexander S ^a   Piatnitski Chekler, Eugene L ^b   Chernisheva, Natalia B ^c   Salamandra, Lev K ^c   Semenov, Victor V ^c  

^a DeCODE Chemistry & Biostructures   (United States)

^b ELI LILLY AND COMPANY   (United States)

^c N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

7,8 Dihydro 1,2,4 triazol 1,5 c pyrimidin 5 yl amines; Angiogenesis; Cyclization; Kinase inhibitor; Knoevenagel condensation; VEGFR 2

Indexed keywords

ALDEHYDE; ALDEHYDE DERIVATIVE; AMINE; ISOTHIOCYANIC ACID; ISOTHIOCYANIC ACID DERIVATIVE; NITRILE; THIOUREA; TRIAZOLE; VASCULOTROPIN INHIBITOR; VASCULOTROPIN RECEPTOR 2;

ARTICLE; CELL ASSAY; CHEMICAL STRUCTURE; CYCLIZATION; ENZYME ACTIVITY; ENZYME ASSAY; KNOEVENAGEL CONDENSATION; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 65549125376     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.04.062     Document Type: Article

References (29)

1. Risau W. Nature 386 (1997) 671-674
2. Klagsbrun M., and Moses M.A. Chem. Biol. 6 (1999) R217-R224
3. Hanahan D., and Folkman J. Cell 86 (1996) 353-364
4. Eskens F. Br. J. Cancer 90 (2004) 1-7
5. Olsson A.-K., Dimberg A., Kreuger J., and Claesson-Welsh L. Nat. Rev. Mol. Cell Biol. 5 (2006) 359-371
6. Zachary I. Biochem. Soc. Trans. 31 (2003) 1171-1177
7. Ferrara N., Hillan K.J., Gerber H.P., and Novotny W. Nat. Rev. Drug Disc. 3 (2004) 391-400
8. Saaristo A., Karpanen T., and Alitalo K. Oncogene 19 (2000) 6122-6199
9. Folkman J. Nat. Med. 1 (1995) 27-31
10. Fuh G., Li B., Crowley C., Cunningham B.C., and Wells J.A. J. Biol. Chem. 273 (1998) 11197-11204
11. Barleon B., Totzke F., Herzog C., Blanke S., Kremmer E., Siemeister G., Marme D., and Martiny-Baron G. J. Biol. Chem. 272 (1997) 10382-10388
12. Kiselyov A.S., Balakin K., and Tkachenko S.E. Expert Opin. Invest. Drugs 16 (2007) 83-107
13. The anti-angiogenic antibody Avastin™ (Bevacizumab, Genentech, San Francisco, CA) has recently been approved for the treatment of colorectal cancer, see. Culy C. Drugs Today 41 (2005) 23-36
14. The anti-angiogenic aptamer Macugen™ (Pegaptanib sodium, Eyetech Pharmaceuticals, New York, NY and Pfizer) has recently been approved to treat neovascular age-related macular degeneration; see. Fine S.L., Martin D.F., and Kirkpatrick P. Nat. Rev. Drug Disc. 4 (2005) 187-188
15. Ciardiello F., Caputo R., Damiano V., Caputo R., Troiani T., Vitagliano D., Carlomagno F., Veneziani B.M., Fontanini G., Bianco A.R., and Tortora G. Clin. Cancer Res. 9 (2003) 1546-1556
16. Drevs J., Konerding M.A., Wolloscheck T., Wedge S.R., Ryan A.J., Ogilvie D.J., and Esser N. Angiogenesis 7 (2005) 347-354
17. Hess-Stumpp H., Haberey M., and Thierauch K.H. Chembiochem 6 (2005) 550-557
18. Manley P.W., Furet P., Bold G., Bruggen J., Mestan J., Meyer T., Schnell C.R., and Wood J. J. Med. Chem. 45 (2002) 5687-5693
19. Piatnitski E.L., Duncton M.A.J., Kiselyov A.S., Katoch-Rouse R., Sherman D., Milligan D.L., Balagtas C., Wong W.C., Kawakami J., and Doody J.F. Bioorg. Med. Chem. Lett. 15 (2005) 4696-4698
20. Duncton M.A.J., Piatnitski E.L., Katoch-Rouse R., Smith L.M., Kiselyov A.S., Milligan D.L., Balagtas C., Wong W.C., Kawakami J., and Doody J.F. Bioorg. Med. Chem. Lett. 16 (2006) 1579-1581
21. Kiselyov A.S., Semenova M., Semenov V.V., and Piatnitski E.L. Chem. Biol. Drug Des. 68 (2006) 250-256
22. Kiselyov A.S., Semenov V.V., and Milligan D.L. Chem. Biol. Drug Des. 68 (2006) 308-314
23. Kiselyov A.S., Piatnitski E.L., Samet A.V., Kisly V.P., and Semenov V.V. Bioorg. Med. Chem. Lett. 17 (2007) 1369-1375 and references cited therein
24. McTigue M.A., Wickersham J.A., Pinko C., Showalter R.E., Parast C.V., Tempczyk-Russell A., Gehring M.R., Mroczkowski B., Kan C.C., Villafranca J.E., and Appelt K. Structure 7 (1999) 319-324
25. Berman H.M., Westbrook J., Feng Z., Gilliland G., Bhat T.N., Weissig H., Shindyalov I.N., and Bourne P.E. Nucleic Acids Res. 28 (2000) 235-242
26. Bahceci S., Yueksek H., and Serdar M. Indian J. Chem B 44B (2005) 568-572
27. Pohl M., Bechstein U., Paetzel M., Liebscher J., and Jones P.G. J. fuer Praktische Chemie/Chemiker-Zeitung 3347 (1992) 630-636
28. Shishoo C.J., Devani M.B., Ullas G.V., Ananthan S., and Bhadti V.S. J. Heterocycl. Chem. 24 (1987) 1125-1129
29. Gatta F., Del Guidice M.R., Borioni A., Mustazza C., and Fazio C. J. Heterocycl. Chem. 31 (1994) 1171-1176