Design and synthesis of novel Gefitinib analogues with improved anti-tumor activity

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 11, 2010, Pages 3812-3822

  Wu, Xiaoqing ^a,b   Li, Mingdong ^a   Qu, Yang ^b   Tang, Wenhua ^b   Zheng, Youguang ^a   Lian, Jiqin ^b   Ji, Min ^a   Xu, Liang ^b  

^a SOUTHEAST UNIVERSITY   (China)

^b UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

4 Benzothienyl amino quinazolines; Apoptosis; Cancer cells; Gefitinib; Receptor tyrosine kinase

Indexed keywords

ERLOTINIB; ETHYL 5 (6 (3 (4 ETHYLPIPERAZIN 1 YL)PROPOXY) 7 METHOXYQUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (6 (3 (DIETHYLAMINO)PROPOXY) 7 METHOXYQUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (6 (3 (DIMETHYLAMINO)PROPOXY) 7 METHOXYQUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (6 METHOXY 6 (7 MORPHOLINOPROPOXY)QUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (6 METHOXY 7 (3 (2 METHYLPIPERIDIN 1 YL)PROPOXY) QUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (6 METHOXY 7 (3 (4 METHYLPIPERAZIN 1 YL)PROPOXY) QUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (6 METHOXY 7 (3 (4 METHYLPIPERIDIN 1 YL)PROPOXY) QUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (6 METHOXY 7 (3 (4 PHENYLPIPERAZIN 1 YL)PROPOXY) QUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (6 METHOXY 7 (3 (PIPERIDIN 1 YL)PROPOXY)QUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (6 METHOXY 7 (3 (PYRROLIDIN 1 YL)PROPOXY)QUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (7 (3 (4 ETHYLPIPERAZIN 1 YL)PROPOXY) 6 METHOXYQUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (7 (3 (DIETHYLAMINO)PROPOXY) 6 METHOXYQUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (7 (3 (DIMETHYLAMINO)PROPOXY) 6 METHOXYQUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (7 METHOXY 6 (3 (2 METHYLPIPERIDIN 1 YL)PROPOXY) QUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (7 METHOXY 6 (3 (4 METHYLPIPERAZIN 1 YL)PROPOXY) QUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (7 METHOXY 6 (3 (4 METHYLPIPERIDIN 1 YL)PROPOXY) QUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (7 METHOXY 6 (3 (4 PHENYLPIPERAZIN 1 YL)PROPOXY) QUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (7 METHOXY 6 (3 (PIPERIDIN 1 YL)PROPOXY)QUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (7 METHOXY 6 (3 (PYRROLIDIN 1 YL)PROPOXY)QUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; ETHYL 5 (7 METHOXY 6 (3 MORPHOLINOPROPOXY)QUINAZOLIN 4 YLAMINO)BENZO[B]THIOPHENE 2 CARBOXYLATE; GEFITINIB; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CARCINOGENESIS; CONTROLLED STUDY; CYTOTOXICITY; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; FEMALE; GROWTH INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG DESIGN; HUMANS; QUINAZOLINES; RECEPTOR, EPIDERMAL GROWTH FACTOR; RECEPTOR, ERBB-2;

EID: 77953325590     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.04.046     Document Type: Article

References (29)

1. Hynes N.E., and Lane H.A. Nat. Rev. Cancer 5 (2005) 341
2. Yarden Y., and Sliwkowski M.X. Nat. Rev. Mol. Cell Biol. 2 (2001) 127
3. Marshall J. Cancer 107 (2006) 1207
4. Scaltriti M., and Baselga J. Clin. Cancer Res. 12 (2006) 5268
5. Velu T.J. Mol. Cell. Endocrinol. 70 (1990) 205
6. Uberall I., Kolar Z., Trojanec R., Berkovcova J., and Hajduch M. Exp. Mol. Pathol. 84 (2008) 79
7. Cohen M.H., Williams G.A., Sridhara R., Chen G., and Pazdur R. Oncologist 8 (2003) 303
8. Cohen M.H., Johnson J.R., Chen Y.F., Sridhara R., and Pazdur R. Oncologist 10 (2005) 461
9. Kris M.G., Natale R.B., Herbst R.S., Lynch Jr. T.J., Prager D., Belani C.P., Schiller J.H., Kelly K., Spiridonidis H., Sandler A., Albain K.S., Cella D., Wolf M.K., Averbuch S.D., Ochs J.J., and Kay A.C. JAMA 290 (2003) 2149
10. Fukuoka M., Yano S., Giaccone G., Tamura T., Nakagawa K., Douillard J.Y., Nishiwaki Y., Vansteenkiste J., Kudoh S., Rischin D., Eek R., Horai T., Noda K., Takata I., Smit E., Averbuch S., Macleod A., Feyereislova A., Dong R.P., and Baselga J. J. Clin. Oncol. 21 (2003) 2237
11. Shepherd F.A., Rodrigues Pereira J., Ciuleanu T., Tan E.H., Hirsh V., Thongprasert S., Campos D., Maoleekoonpiroj S., Smylie M., Martins R., van Kooten M., Dediu M., Findlay B., Tu D., Johnston D., Bezjak A., Clark G., Santabarbara P., and Seymour L. N. Eng. J. Med. 353 (2005) 123
12. Kobayashi S., Boggon T.J., Dayaram T., Janne P.A., Kocher O., Meyerson M., Johnson B.E., Eck M.J., Tenen D.G., and Halmos B. N. Eng. J. Med. 352 (2005) 786
13. Rewcastle G.W., Denny W.A., Bridges A.J., Zhou H.R., Cody D.R., Mcmichael A., and Fry D.W. J. Med. Chem. 38 (1995) 3482
14. Bridges A.J., Zhou H., Cody D.R., Rewcastle G.W., McMichael A., Showalter H.D.H., Fry D.W., Kraker A.J., and Denny W.A. J. Med. Chem. 39 (1996) 267
15. Smaill J.B., Palmer B.D., Rewcastle G.W., Denny W.A., McNamara D.J., Dobrusin E.M., Bridges A.J., Zhou H.R., Showalter H.D.H., Winters R.T., Leopold W.R., Fry D.W., Nelson J.M., Slintak V., Elliot W.L., Roberts B.J., Vincent P.W., and Patmore S.J. J. Med. Chem. 42 (1999) 1803
16. Smaill J.B., Rewcastle G.W., Bridges A.J., Zhou H.R., Showalter H.D.H., Fry D.W., Nelson J.M., Sherwood V., Elliott W.L., Vincent P.W., DeJohn D.E., Loo J.A., Greis K.D., Chan O.H., Reyner E.L., Lipka E., and Denny W.A. J. Med. Chem. 43 (2000) 3199
17. Petrov K.G., Zhang Y.M., Carter M., Cockerill G.S., Dickerson S., Gauthier C.A., Guo Y., Mook Jr. R.A., Rusnak D.W., Walker A.L., Wood E.R., and Lackey K.E. Bioorg. Med. Chem. Lett. 16 (2006) 4686
18. Wissner A., Berger D.M., Boschelli D.H., Floyd Jr. M.B., Greenberger L.M., Gruber B.C., Johnson B.D., Mamuya N., Nilakantan R., Reich M.F., Shen R., Tsou H.R., Upeslacis E., Wang Y.F., Wu B., Ye F., and Zhang N. J. Med. Chem. 43 (2000) 3244
19. Zhang Y.M., Cockerill S., Guntrip S.B., Rusnak D., Smith K., Vanderwall D., Wood E., and Lackey K. Bioorg. Med. Chem. Lett. 14 (2004) 111
20. Assefa H., Kamath S., and Buolamwini J.K. J. Comput. Aided Mol. Des. 17 (2003) 475
21. Ballard P., Bradbury R.H., Harris C.S., Hennequin L.F., Hickinson M., Kettle J.G., Kendrew J., Klinowska T., Ogilvie D.J., Pearson S.E., Williams E.J., and Wilson I. Bioorg. Med. Chem. Lett. 16 (2006) 4908
22. Telliez A., Desroses M., Pommery N., Briand O., Farce A., Laconde G., Lemoine A., Depreux P., and Henichart J.P. ChemMedChem 2 (2007) 318
23. Yano S., Wang W., Li Q., Matsumoto K., Sakurama H., Nakamura T., Ogino H., Kakiuchi S., Hanibuchi M., Nishioka Y., Uehara H., Mitsudomi T., Yatabe Y., and Sone S. Cancer Res. 68 (2008) 9479
24. Karamouzis M.V., Konstantinopoulos P.A., and Papavassiliou A.G. Lancet Oncol. 10 (2009) 709
25. Meng Y., Tang W., Dai Y., Wu X., Liu M., Ji Q., Ji M., Pienta K., Lawrence T., and Xu L. Mol. Cancer Ther. 7 (2008) 2192
26. Xu L., Yang D., Wang S., Tang W., Liu M., Davis M., Chen J., Rae J.M., Lawrence T., and Lippman M.E. Mol. Cancer Ther. 4 (2005) 197
27. Dai Y., Liu M., Tang W., DeSano J., Burstein E., Davis M., Pienta K., Lawrence T., and Xu L. Clin. Cancer Res. 14 (2008) 7701
28. Dai Y., DeSano J.T., Meng Y., Ji Q., Ljungman M., Lawrence T.S., and Xu L. Int. J. Radiat. Oncol. Biol. Phys. 74 (2009) 1217
29. Ji Q., Hao X., Zhang M., Tang W., Yang M., Li L., Xiang D., Desano J.T., Bommer G.T., Fan D., Fearon E.R., Lawrence T.S., and Xu L. PLoS One 4 (2009) e6816