8-THP-DHI analogs as potent Type I dual TIE-2/VEGF-R2 receptor tyrosine kinase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 11, 2010, Pages 3356-3360

  Hudkins, Robert L ^a   Zulli, Allison L ^a   Underiner, Ted L ^a   Angeles, Thelma S ^a   Aimone, Lisa D ^a   Meyer, Sheryl L ^a   Pauletti, Daniel ^a   Chang, Hong ^a   Fedorov, Elena V ^b   Almo, Steven C ^b   Fedorov, Alexander A ^b   Ruggeri, Bruce A ^a  

^a CEPHALON INC   (United States)

^b ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

Author keywords

Angiogenesis; Kinase inhibitor; TIE 2; VEGF R2

Indexed keywords

8 (2 TETRAHYDROPYRANYL) 12,13 DIHYDROINDAZOLO[5,4 A]PYRROLO[3,4 C]CARBAZOLE; ANGIOPOIETIN RECEPTOR; PROTEIN TYROSINE KINASE INHIBITOR; SORAFENIB; SUNITINIB; UNCLASSIFIED DRUG; VASCULOTROPIN RECEPTOR 2;

ARTICLE; DRUG POTENCY; DRUG SYNTHESIS; STRUCTURE ACTIVITY RELATION; TUMOR MODEL; X RAY CRYSTALLOGRAPHY;

ANIMALS; CELLS, CULTURED; CRYSTALLOGRAPHY, X-RAY; HUMANS; MODELS, MOLECULAR; PROTEIN KINASE INHIBITORS; RATS; RECEPTOR, TIE-2; STRUCTURE-ACTIVITY RELATIONSHIP; VASCULAR ENDOTHELIAL GROWTH FACTOR RECEPTOR-2;

EID: 77953293962     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.04.021     Document Type: Article

References (34)

1. Folkman J. N. Engl. J. Med. 285 (1971) 1182-1186
2. Folkman J., and Shing Y. J. Biol. Chem. 267 (1992) 10931-10934
3. Carmeliet P., and Jain R.K. Nature 407 (2000) 249-257
4. Folkman J. Nat. Med. 1 (1995) 27
5. Hurwitz H., Fehrenbacher L., Novotny W., Cartwright T., Hainsworth J., Heim W., Berlin J., Baron A., Griffing S., Holmgren E., Ferrara N., Fyfe G., Rogers B., Ross R., and Kabbinavar F. N. Engl. J. Med. 350 (2004) 2335
6. Escudier B., Eisen T., Stadler W.M., Szczylik C., Oudard S., Staehler M., Negrier S., Chevreau C., Desai A.A., Rolland F., Demkow T., Hutson T.E., Gore M., Anderson S., Hofilena G., Shan M., Pena C., Lathia C., and Bukowski R.M. J. Clin. Oncol. 27 (2009) 3312
7. Demetri G.D., van Oosterom A.T., Garrett C.R., Blackstein M.E., Shah M.H., Verweij J., McArthur G., Judson I.R., Heinrich M.C., Morgan J.A., Desai J., Fletcher C.D., George S., Bello C.L., Huang X., Baum C.M., and Casali P.G. Lancet 368 (2006) 1329
8. Bergers G., and Benjamin L.E. Nat. Rev. Cancer 3 (2003) 401
9. Lin P., Buxton J.A., Acheson A., Radziejewski C., Maisonpierre P.C., Yancopoulos G.D., Channon K.M., Hale L.P., Dewhirst M.W., George S.E., and Peters K.G. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 8829
10. Cristofanilli M., Charnsangavej C., and Hortobagyi G.N. Nat. Rev. Drug Disc. 1 (2002) 415
11. Jones N., LLjin K., Dumount D., and Alitalo K. Nat. Rev. Mol. Cell Biol. 2 (2001) 257
12. Lin P., Polverini P., Dewhirst M., Shan S., Rao P.S., and Peters K.G. J. Clin. Invest. 100 (1997) 2072
13. Mi J., Sarraf-Yazdi S., Cao Y., Dewhirst M.W., and Clary B.M. Proc. Soc. Am. Assoc. Cancer Res. 44 (2003) 5747
14. Shim W.S.N., Teh M., Mack P.O.P., and Ge R. Int. J. Cancer 94 (2001) 6
15. Stratman A., Acker T., Burger A., Amann K., Risau W., and Plate K.H. Int. J. Cancer 91 (2001) 273
16. Jendreyko N., Popkov M., Rader C., and Barbas C.F. Proc. Natl. Acad. Sci. U.S.A. 102 (2005) 8293
17. Popkov M., Jendreyko N., McGavern D.B., Rader C., and Barbas C.F. Cancer Res. 65 (2005) 972
18. Beebe J.S., Jani J.P., Knauth E., Goodwin P., Higdon C., Rossi A.M., Emerson E., Finkelstein M., Floyd E., Harriman S., Atherton J., Hillerman S., Soderstrom C., Kou K., Gant T., Noe M.C., Foster B., Rastinejad F., Marx M.A., Schaeffer T., Whalen P.M., and Roberts W.G. Cancer Res. 63 (2003) 7301
19. Hasegawa M., Nishigaki N., Washio Y., Kano K., Harris P.A., Sato H., Mori I., West R.I., Shibahara M., Toyoda H., Wang L., Nolte R.T., Veal J.M., and Cheung M. J. Med. Chem. 50 (2007) 4453
20. Ji Z., Ahmed A.A., Albert D.H., Bouska J.J., Bousquet P.F., Cunha G.A., Glaser K.B., Guo J., Li J., Marcotte P.A., Moskey M.D., Pease L.J., Stewart K.D., Yates M., Davidsen S.K., and Michaelides M.R. Bioorg. Med. Chem. Lett. 16 (2006) 4326
21. Miyazaki Y., Tang J., Maeda Y., Nakano M., Wang L., Nolte R.T., Sato H., Sugai M., Okamoto Y., Truesdale A.T., Hassler D.F., Nartey E.N., Patrick D.R., Ho M.L., and Ozawa K. Bioorg. Med. Chem. Lett. 17 (2007) 1773
22. Miyazaki Y., Matsunaga S., Tang J., Maeda Y., Nakano M., Philippe R.J., Shibahara M., Liu W., Sato H., Wang L., and Nolte R.T. Bioorg. Med. Chem. Lett. 15 (2005) 2203
23. Gingrich D.E., Reddy D.R., Iqbal M.A., Singh J., Aimone L.D., Angeles T.S., Albom M., Yang S., Meyer S., Ator M., Robinson C., Ruggeri B.A., Dionne C.A., Vaught J.L., Mallamo J.P., and Hudkins R.L. J. Med. Chem. 46 (2003) 5375
24. Ruggeri B., Singh J., Gingrich D., Angeles T., Albom M., Chang H., Robinson C., Hunter K., Dobrzanski P., Jones-Bolin S., Aimone L., Klein-Szanto A., Herbert J.-M., Bono F., Schaeffer P., Casellas P., Bourie B., Pili R., Isaacs J., Ator M., Hudkins R., Vaught J., Mallamo J., and Dionne C. Cancer Res. 63 (2003) 5978
25. Becknell N.C., Zulli A.L., Angeles T.S., Yang S., Albom M.S., Aimone L.D., Robinson C., Chang H., and Hudkins R.L. Bioorg. Med. Chem. Lett. 16 (2006) 5368
26. Reddeppareddy D., Zulli A.L., Bacon E.R., Underiner T.L., Robinson C., Chang H., Miknyoczki S., Grobelny J., Ruggeri B., Yang S., Albom M.S., Angeles T., Aimone L.A., and Hudkins R.L. Bioorg. Med. Chem. Lett. 18 (2008) 1916
27. Underiner T.L., Ruggeri B., Aimone L.A., Albom M., Angeles T., Chang H., Hudkins R.L., Hunter K., Josef K., Robinson C., Weinberg L., and Yang S. Zulli, A.Bioorg. Med. Chem. Lett. 18 (2008) 2368
28. Tao M., Park C.-H., Josef K.A., and Hudkins R.L. J. Heterocycl. Chem. 46 (2009) 1185
29. Hudkins, R. L.; Zulli, A. L.; Reddy, D. R.; Gingrich, D. E.; Tao, M.; Becknell, N. C.; Diebold, J. L.; Underiner, T. L. US 7,169,802, 2007.
30. Josef K.A., Reddeppareddy D., Tao M., and Hudkins R.L. J. Heterocycl. Chem. 43 (2006) 719
31. Reddy D.R., Tao M., Josef K.A., Bacon E.R., and Hudkins R.L. J. Heterocycl. Chem. 44 (2007) 437
32. Kissinger C.R., Gehlhaar D.K., and Fogel D.B. Acta Crystallogr., Sect. D 55 (1999) 484
33. Brunger A.T., Adams P.D., Clore G.M., DeLAno W.L., Gros P., Grosse-Kunstleve R.W., Jiang J.S., Kuszewski J., Nilges M., Pannu N.S., Read R.J., Rice L.M., Simonson T., and Warren G.L. Acta Crystallogr., Sect. D 54 (1998) 905
34. Jones A.T. Meth. Enzymol. 115 (1985) 157