Design and synthesis of new stabilized combi-triazenes for targeting solid tumors expressing the epidermal growth factor receptor (EGFR) or its closest homologue HER2

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 18, 2009, Pages 5505-5509

  Rachid, Zakaria ^a   MacPhee, Meaghan ^a   Williams, Christopher ^b   Todorova, Margarita ^a   Jean Claude, Bertrand Jacques ^a  

^a Cancer Drug Research Laboratory   (Canada)

^b INSTITUTE FOR RESEARCH IN IMMUNOLOGY AND CANCER   (Canada)

Author keywords

Combi triazenes; EGFR; HER2; Quinazoline

Indexed keywords

AMINOQUINAZOLINE; ANTINEOPLASTIC AGENT; CANERTINIB; CARBAMIC ACID DERIVATIVE; EPIDERMAL GROWTH FACTOR RECEPTOR; EPIDERMAL GROWTH FACTOR RECEPTOR 2; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE INHIBITOR; GEFITINIB; QUINAZOLINE DERIVATIVE; RB 107; RB 24; TRIAZENE DERIVATIVE; UNCLASSIFIED DRUG; ZRS 1;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CONTROLLED STUDY; DNA DAMAGE; DRUG DESIGN; DRUG MECHANISM; DRUG STABILITY; DRUG SYNTHESIS; DRUG TARGETING; HUMAN; HUMAN CELL; IC 50; NONHUMAN; PROTEIN EXPRESSION; SOLID TUMOR; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL LINE, TUMOR; CELL PROLIFERATION; FEMALE; HUMANS; MICE; MODELS, MOLECULAR; NIH 3T3 CELLS; PROTEIN BINDING; RECEPTOR, EPIDERMAL GROWTH FACTOR; RECEPTOR, ERBB-2; TRIAZENES;

EID: 69049097421     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.05.060     Document Type: Article

References (25)

1. Lynch T.J., Bell D.W., Sordella R., Gurubhagavatula S., Okimoto R.A., Brannigan B.W., Harris P.L., Haserlat S.M., Supko J.G., Haluska F.G., Louis D.N., Christiani D.C., Settleman J., and Haber D.A. N. Eng. J. Med. 350 (2004) 2129
2. Pao W., and Miller V.A. J. Clin. Oncol. 23 (2005) 2556
3. Mitsudomi T., Kosaka T., Endoh H., Horio Y., Hida T., Mori S., Hatooka S., Shinoda M., Takahashi T., and Yatabe Y. J. Clin. Oncol. 23 (2005) 2513
4. Giaccone G., and Rodriguez J.A. Nat. Clin. Pract. Oncol. 2 (2005) 554
5. Brahimi F., Matheson S.L., Dudouit F., McNamee J.P., Tari A.M., and Jean-Claude B.J. J. Pharmacol. Exp. Ther. 303 (2002) 238
6. Matheson S.L., McNamee J.P., Wang T., Alaoui-Jamali M.A., Tari A.M., and Jean-Claude B.J. J. Pharmacol. Exp. Ther. 311 (2004) 1163
7. Gonzales A.J., Hook K.E., Althaus I.W., Ellis P.A., Trachet E., Delaney A.M., Harvey P.J., Ellis T.A., Amato D.M., Nelson J.M., Fry D.W., Zhu T., Loi C.-M., Fakhoury S.A., Schlosser K.M., Sexton K.E., Winters R.T., Reed J.E., Bridges A.J., Lettiere D.J., Baker D.A., Yang J., Lee H.T., Tecle H., and Vincent P.W. Mol. Cancer Ther. 7 (2008) 1880
8. Banerjee R., Rachid Z., Qiu Q., McNamee J.P., Tari A.M., and Jean-Claude B.J. Br. J. Cancer 91 (2004) 1066
9. Banerjee R., Rachid Z., McNamee J., and Jean-Claude B.J. J. Med. Chem. 46 (2003) 5546
10. Matheson S.L., McNamee J., and Jean-Claude B.J. J. Pharmacol. Exp. Ther. 296 (2001) 832
11. Brahimi F., Rachid Z., McNamee J.P., Alaoui-Jamali M.A., Tari A.M., and Jean-Claude B.J. Biochem. Pharm. 70 (2005) 511
12. Qiu Q., Larroque A.L., Gibbs B.F., Fang J.Y., Lakhrissi Y., Soucy J.-P., Mzengeza S., Rachid Z., and Jean-Claude B.J. Drug Metab. Lett. 3 (2009) 1
13. Tsou H.R., Mamuya N., Johnson B.D., Reich M.F., Gruber B.C., Ye F., Nilakantan R., Shen R., Discafani C., DeBlanc R., Davis R., Koehn F.E., Greenberger L.M., Wang Y.F., and Wissner A. J. Med. Chem. 44 (2001) 2719
14. Rewcastle G.W., Bridges A.J., Fry D.W., Rubin J.R., and Denny W.A. J. Med. Chem. 40 (1997) 1820
15. Rewcastle G.W., Denny W.A., Bridges A.J., Zhou H., Cody D.R., McMichael A., and Fry D.W. J. Med. Chem. 38 (1995) 3482
16. Rewcastle G.W., Murray D.K., Elliott W.L., Fry D.W., Howard C.T., Nelson J.M., Roberts B.J., Vincent P.W., Showalter H.D.H., Winters R.T., and Denny W.A. J. Med. Chem. 41 (1998) 742
17. Rewcastle G.W., Palmer B.D., Thompson A.M., Bridges A.J., Cody D.R., Zhou H., Fry D.W., McMichael A., Kraker A.J., and Denny W.A. J. Med. Chem. 39 (1996) 1823
18. Rachid Z., Brahimi F., Qiu Q., Williams C., Hartley J.M., Hartley J.A., and Jean-Claude B.J. J. Med. Chem. 50 (2007) 2605
19. Carvalho E., Francisco A.P., Iley J., and Rosa E. Bioorg. Med. Chem. 8 (2000) 1719
20. Brahimi F., Rachid Z., Qiu Q., McNamee J.P., Li Y.-J., Tari A.M., and Jean-Claude B.J. Int. J. Cancer 112 (2004) 484
21. Matheson S.L., McNamee J.P., and Jean-Claude B.J. Cancer Chemother. Pharmcol. 51 (2003) 11
22. Stamos J., Sliwkowski M.X., and Eigenbrot C. J. Biol. Chem. 277 (2002) 46265
23. moe software (Version 2006.07) available from Chemical Computing Group Inc., S. S. W., Montreal, Quebec, Canada. www.chemcomp.com.
24. Macphee, M.; Rachid, Z.; Todorova, M.; Qui, Q.; Jean-claude, B. submitted for publication.
25. Rachid Z., Brahimi F., Katsoulas A., Teoh N., and Jean-Claude B.J. J. Med. Chem. 46 (2003) 4313