(1,2,3-Triazol-4-yl)benzenamines: Synthesis and activity against VEGF receptors 1 and 2

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 5, 2009, Pages 1344-1348

  Kiselyov, Alexander S ^a   Semenova, Marina ^b   Semenov, Victor V ^c  

^a DeCODE Chemistry & Biostructures   (United States)

^b KOL TSOV INSTITUTE OF DEVELOPMENTAL BIOLOGY   (Russian Federation)

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

Author keywords

(1,2,3 Triazol 4 yl) benzenamines; Angiogenesis; ATP competitive kinase inhibitors; Vascular endothelial growth factor receptor 2; VEGFR 2

Indexed keywords

2 [1 (3 CHLOROPHENYL) 1H 1,2,3 TRIAZOL 4 YL] N (PYRIDIN 4 YLMETHYL)BENZENAMINE; [1 (3 CHLOROPHENYL) 1H 1,2,3 TRIAZOL 4 YL] N (QUINOLIN 4 YLMETHYL)BENZENAMINE; BENZENE DERIVATIVE; MOTESANIB; N (PYRIDIN 4 YLMETHYL) 2 [1 [3 (TRIFLUOROMETHYL)PHENYL] 1H 1,2,3 TRIAZOL 4YL]BENZENAMINE; N [(1H IMIDAZOL 4 YL)METHYL] 2 [1 (3 CHLOROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]BENZENAMINE; UNCLASSIFIED DRUG; VASCULOTROPIN RECEPTOR 1; VASCULOTROPIN RECEPTOR 2; VATALANIB;

ARTICLE; CELL ASSAY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ASSAY; IC 50; INHIBITION KINETICS; RECEPTOR BLOCKING;

BENZENE DERIVATIVES; BINDING SITES; HUMANS; TRIAZOLES; VASCULAR ENDOTHELIAL GROWTH FACTOR RECEPTOR-1; VASCULAR ENDOTHELIAL GROWTH FACTOR RECEPTOR-2;

EID: 60449096371     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.01.046     Document Type: Article

References (23)

1. Bailar III J.C., and Gornick H.L. N. Engl. J. Med. 336 (1997) 1569
2. Boehm T., Folkman J., and Browder T. Nature 390 (1997) 404
3. Risau W. Nature 386 (1997) 671
4. Klagsbrun M., and Moses M.A. Chem. Biol. 6 (1999) R217
5. Hanahan D., and Folkman J. Cell 86 (1996) 353
6. Olsson A.-K., Dimberg A., Kreuger J., and Claesson-Welsh L. Nat. Rev. Mol. Cell Biol. 5 (2006) 359
7. Zachary I. Biochem. Soc. Trans. 31 (2003) 1171
8. Perona R. Clin. Transl. Oncol. 8 (2006) 77
9. Jin T., Nakatani H., and Taguchi T. World J. Gastroenterol. 12 (2006) 703
10. Itakura J., Ishiwata T., and Shen B. Int. J. Cancer 85 (2000) 27
11. Saaristo A., Karpanen T., and Alitalo K. Oncogene 19 (2000) 6122
12. Ferrara N., Hillan K.J., Gerber H.P., and Novotny W. Nature Rev. Drug Discov. 3 (2004) 391
13. Fine S.L., Martin D.F., and Kirkpatrick P. Nature Rev. Drug Disc. 4 (2005) 187
14. Culy C. Drugs Today 41 (2005) 23
15. Bold G., Altmann K.-H., Jorg F., Lang M., Manley P.W., Traxler P., Wietfeld B., Bruggen J., Buchdunger E., Cozens R., Ferrari S., Pascal F., Hofmann F., Martiny-Baron G., Mestan J., Rosel J., Sills M., Stover D., Acemoglu F., Boss E., Emmenegger R., Lasser L., Masso E., Roth R., Schlachter C., Vetterli W., Wyss D., and Wood J.M. J. Med. Chem. 43 (2000) 2310
16. Chang, Y.S.; Cortes, C.; Polony, B. Proc. Am. Assoc. Cancer Res. (AACR) 2005, 46, Abstr 2030.
17. Manley P.W., Furet P., Bold G., Brüggen J., Mestan J., Meyer T., Schnell C., and Wood J. J. Med. Chem. 45 (2002) 5697
18. Kaufman S., Starnes C., and Coxon A. Proc. Am. Assoc. Cancer Res. (AACR) 47 (2006) Abstr 3792
19. Kiselyov A.S., Piatnitski L.E., Samet A.V., Kisly V.P., and Semenov V.V. Bioorg. Med. Chem. Lett. 17 (2007) 1369 and references cited therein
20. Kiselyov A.S., Balakin K., and Tkachenko S.E. Expert Opin. Invest. Drugs 16 (2007) 83
21. 6O: C, 54.80; H, 3.99; N, 25.56. Found: C, 54.59; H, 3.82, N, 25.38.
22. 2, 2 mM DTT, 1 mg/ml BSA) containing 0.5 mmol pGAT-biotin and 3-4 ng KDR enzyme is added to each well. After 5-10 min preincubation, the kinase reaction is initiated by the addition of 10 μl of 10 μM ATP in reaction buffer, after which the plate is incubated at room temperature for 45 min. The reaction is stopped by addition of 50 μl of KF buffer, (50 mM Hepes, pH 7.5, 0.5 M KF, 1 mg/ml BSA) containing 100 mM EDTA and 0.36 μg/ml PY20 K (Eu-cryptate labeled anti-phosphotyrosine antibody, CIS bio international) is added and after an additional 2 h incubation at room temperature, the plate is read in a RUBYstar HTRF Reader.
23. 4, absorbance was measured at 450 nm.