Design, synthesis and biological evaluation of novel 6-alkenylamides substituted of 4-anilinothieno[2,3-d]pyrimidines as irreversible epidermal growth factor receptor inhibitors

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 7, 2014, Pages 2366-2378

  Ji, Xun ^a,b   Peng, Ting ^a   Zhang, Xu ^a   Li, Jian ^a   Yang, Wei ^a   Tong, Linjiang ^a   Qu, Rong ^a   Jiang, Hualiang ^a,b   Ding, Jian ^a   Xie, Hua ^a   Liu, Hong ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

EGFR T790M L858R; Irreversible EGFR inhibitor; Thieno 2,3 d pyrimidines

Indexed keywords

2 CHLORO N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 2 [4 (2 HYDROXYETHYL)PIPERAZIN 1 YL]ACETAMIDE; 4 ANILINOTHIENO[2,3 D]PYRIMIDINE DERIVATIVE; AFATINIB; ALLYL [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 2 [4 (2 HYDROXYETHYL)PIPERAZIN 1 YL]CARBAMATE; EPIDERMAL GROWTH FACTOR RECEPTOR; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE INHIBITOR; GEFITINIB; METHYL 3 [[4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL]AMINO] 3 OXOPROPANOATE; METHYL 5 [[4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL]AMINO] 5 OXOPROPANOATE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 2 (4 METHYLPIPERAZIN 1 YL)ACETAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 2 ETHYLBUTANAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 2 [4 (2 HYDROXYETHYL)PIPERAZIN 1 YL] 2 METHYLBUT 2 ENAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 2 [4 (2 HYDROXYETHYL)PIPERAZIN 1 YL]ACETAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 2 [4 (2 HYDROXYETHYL)PIPERIDIN 1 YL]ACETAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 2 [[2 (DIMETHYLAMINO)ETHYLMETHYL]AMINO]ACETAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 2 [[3 (DIMETHYLAMINO)PROPYL](METHYL)AMINO]ACETAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 4 (DIETHYLAMINO)BUT 2 ENAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 4 (DIMETHYLAMINO)BUT 2 ENAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 4 (DIMETHYLAMINO)BUTANAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 4 [(2 METHOXYETHYL)AMINO]BUT 2 ENAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 4 [(OXETAN 3 YLMETHYL)AMINO]BUT 2 ENAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 4 [(PYRIMIDIN 2 YLMETHYL)AMINO]BUT 2 ENAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 4 [(TETRAHYDRO 2H PYRAN 4 YL)AMINO]BUT 2 ENAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 4 [[2 (METHYLSULFONYL)ETHYL]AMINO]BUT 2 ENAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL] 4 [[3 (DIMETHYLAMINO)PROPYL]AMINO]BUT 2 ENAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL]ACRYLAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL]CYCLOPENTANECARBOXAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]THIENO[2,3 D]PYRIMIDIN 6 YL]PENTANAMIDE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; AMIDE; ANTINEOPLASTIC AGENT; EGFR PROTEIN, HUMAN; PROTEIN KINASE INHIBITOR; THIOPHENE DERIVATIVE;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; AUTOPHOSPHORYLATION; CANCER CELL CULTURE; CARCINOMA CELL; CELL STRAIN A431; CELL STRAIN NCI H1975; CONCENTRATION RESPONSE; CONTROLLED STUDY; DILUTION; DRUG DESIGN; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; LUNG ADENOCARCINOMA; PHARMACOLOGICAL BLOCKING; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION; WILD TYPE; ANTAGONISTS AND INHIBITORS; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; DRUG SCREENING; GENETICS; SYNTHESIS; TUMOR CELL LINE;

AMIDES; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR STRUCTURE; PROTEIN KINASE INHIBITORS; PYRIMIDINES; RECEPTOR, EPIDERMAL GROWTH FACTOR; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES;

EID: 84897371143     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.01.035     Document Type: Article

References (45)

1. A. Citri, and Y. Yarden Nat. Rev. Mol. Cell Biol. 7 2006 505
2. O. Segatto, S. Anastasi, and S. Alemà J. Cell Sci. 124 2011 1785
3. J. Schlessinger Cell 103 2000 211
4. M.A. Olayioye, R.M. Neve, H.A. Lane, and N.E. Hynes EMBO J. 19 2000 3159
5. A.W. Burgess, H.S. Cho, C. Eigenbrot, K.M. Ferguson, T.P.J. Garrett, D.J. Leahy, M.A. Lemmon, M.X. Sliwkowski, C.W. Ward, and S. Yokoyama Mol. Cell 12 2003 541
6. R. Saxena, and A. Dwivedi Med. Res. Rev. 32 2012 166
7. E. Iivanainen, and K. Elenius Curr. Vasc. Pharmacol. 8 2010 421
8. M. Dowsett, T. Cooke, L. Ellis, W.J. Gullick, B. Gusterson, E. Mallon, and R. Walker Eur. J. Cancer 36 2000 170
9. H. Kim, and W.J. Muller Exp. Cell Res. 253 1999 78
10. T. Ishikawa, M. Seto, H. Banno, Y. Kawakita, M. Oorui, T. Taniguchi, Y. Ohta, T. Tamura, A. Nakayama, H. Miki, H. Kamiguchi, T. Tanaka, N. Habuka, S. Sogabe, J. Yano, K. Aertgeerts, and K. Kamiyama J. Med. Chem. 54 2011 8030
11. J. Yang, L.J. Wang, J.J. Liu, L. Zhong, R.L. Zheng, Y. Xu, P. Ji, C.H. Zhang, W.J. Wang, X.D. Lin, L.L. Li, Y.Q. Wei, and S.Y. Yang J. Med. Chem. 55 2012 10685
12. A. Wissner, E. Overbeek, M.F. Reich, M.B. Floyd, B.D. Johnson, N. Mamuya, E.C. Rosfjord, C. Discafani, R. Davis, X. Shi, S.K. Rabindran, B.C. Gruber, F. Ye, W.A. Hallett, R. Nilakantan, R. Shen, Y.F. Wang, L.M. Greenberger, and H.R. Tsou J. Med. Chem. 46 2003 49
13. J.B. Smaill, B.D. Palmer, G.W. Rewcastle, W.A. Denny, D.J. McNamara, E.M. Dobrusin, A.J. Bridges, H. Zhou, H.D. Showalter, R.T. Winters, W.R. Leopold, D.W. Fry, J.M. Nelson, V. Slintak, W.L. Elliot, B.J. Roberts, P.W. Vincent, and S.J. Patmore J. Med. Chem. 42 1999 1803
14. A.J. Barker, K.H. Gibson, W. Grundy, A.A. Godfrey, J.J. Barlow, M.P. Healy, J.R. Woodburn, S.E. Ashton, B.J. Curry, L. Sarlett, L. Henthorn, and L. Richards Bioorg. Med. Chem. Lett. 11 2001 1911
15. J.D. Moyer, E.G. Barbacci, K.K. Iwata, L. Arnold, B. Boman, A. Cunningham, C. Di Orio, J. Doty, M.J. Morin, M.P. Moyer, M. Neveu, V.A. Pollack, L.R. Pustilnick, M.M. Reynolds, D. Sloan, A. Theleman, and P. Miller Caner Res. 57 1997 4838
16. F. Tan, X. Shen, D. Wang, G. Xie, X. Zhang, L. Ding, Y. Hu, W. He, Y. Wang, and Y. Wang Lung Cancer 76 2012 177
17. E.R. Wood, A.T. Truesdale, O.B. McDonald, D. Yuan, A. Hassell, S.H. Dickerson, B. Ellis, C. Pennisi, E. Horne, K. Lackey, K.J. Alligood, K.D. Rusnak, T.M. Gilmer, and L. Shewchuk Cancer Res. 64 2004 6652
18. K.G. Petrov, Y.M. Zhang, M. Carter, G.S. Cockerill, S. Dickerson, C.A. Gauthier, Y. Guo, R.A. Mook Jr., D.W. Rusnak, A.L. Walker, E.R. Wood, and K.E. Lackey Bioorg. Med. Chem. Lett. 16 2006 4686
19. S. Kobayashi, T.J. Boggon, T. Dayaram, P.A. Jänne, O. Kocher, M. Meyerson, B.E. Johnson, M.J. Eck, D.G. Tenen, and B. Halmos N. Eng. J. Med. 352 2005 786
20. J.A. Engelman, and P.A. Jänne Clin. Cancer Res. 14 2008 2895
21. N. Minkovsky, and A. Berezov Curr. Opin. Invest. Drugs 9 2008 1336
22. F. Solca, G. Dahl, A. Zoephel, G. Bader, M. Sanderson, C. Klein, O. Kraemer, F. Himmelsbach, E. Haaksma, and G.R. Adolf J. Pharmacol. Exp. Ther. 343 2012 342
23. W.J. Slichenmyer, W.L. Elliott, and D.W. Fry Semin. Oncol. 28 2001 80
24. J.B. Smaill, G.W. Rewcastle, J.A. Loo, K.D. Greis, O.H. Chan, E.L. Reyner, E. Lipka, H.D. Showalter, P.W. Vincent, W.L. Elliott, and W.A. Denny J. Med. Chem. 43 2000 1380
25. S.K. Rabindran, C.M. Discafani, E.C. Rosfjord, M. Baxter, M.B. Floyd, J. Golas, W.A. Hallett, B.D. Johnson, D. Nilakantan, E. OverBeek, M.F. Reich, R. Shen, X. Shi, H.R. Tsou, Y.F. Wang, and A. Wissner Cancer Res. 64 2004 3958
26. H.R. Tsou, E.G. Overbeek-Klumpers, W.A. Hallett, M.F. Reich, M.B. Floyd, B.D. Johnson, R.S. Michalak, R. Nilakantan, C. Discafani, J. Golas, S.K. Rabindran, R. Shen, X. Shi, Y.F. Wang, J. Upeslacis, and A. Wissner J. Med. Chem. 48 2005 1107
27. http://www.fda.gov/newsevents/newsroom/pressannouncements/ucm360499.htm.
28. X. Zhang, T. Peng, X. Ji, J. Li, L. Tong, Z. Li, W. Yang, Y. Xu, M. Li, J. Ding, H. Jiang, H. Xie, and H. Liu Bioorg. Med. Chem. 21 2013 7988
29. M.B. Dewal, A.S. Wani, C. Vidaillac, D. Oupický, M.J. Rybak, and S.M. Firestine Eur. J. Med. Chem. 51 2012 145
30. Y. Kotaiah, N. Harikrishna, K. Nagaraju, and C. VenkataRao Eur. J. Med. Chem. 58 2012 340
31. X. Deng, B. Okram, Q. Ding, J. Zhang, Y. Choi, F.J. Adrián, A. Wojciechowski, G. Zhang, J. Che, B. Bursulaya, S.W. Cowan-Jacob, G. Rummel, T. Sim, and N.S. Gray J. Med. Chem. 53 2010 6934
32. A. Zhao, X. Gao, Y. Wang, J. Ai, Y. Wang, Y. Chen, M. Geng, and A. Zhang Bioorg. Med. Chem. 19 2011 3906
33. T.R. Rheault, T.R. Caferro, S.H. Dickerson, K.H. Donaldson, M.D. Gaul, A.S. Goetz, R.J. Mullin, O.B. McDonald, K.G. Petrov, D.W. Rusnak, L.M. Shewchuk, G.M. Spehar, A.T. Truesdale, D.E. Vanderwall, E.R. Wood, and D.E. Uehling Bioorg. Med. Chem. Lett. 19 2009 817
34. C.H. Yun, T.J. Boggon, Y. Li, M.S. Woo, H. Greulich, M. Meyerson, and M.J. Eck Cancer Cell 11 2007 217
35. J. Wang, M. Sánchez-Roselló, J.L. Aceña, C. DelPozo, A.E. Sorochinsky, S. Fustero, V.A. Soloshonok, and H. Liu Chem. Rev. 2013 Article ASAP
36. J.L. Aceña, A.E. Sorochinsky, H. Moriwaki, T. Sato, and V.A. Soloshonok J. Fluorine Chem. 155 2013 21
37. K.V. Turcheniuk, V.P. Kukhar, G.V. Röschenthaler, J.L. Aceña, V.A. Soloshonok, and A.E. Sorochinsky RSC Adv. 3 2013 6693
38. J.L. Han, A.E. Sorochinsky, T. Ono, and V.A. Soloshonok Curr. Org. Synth. 8 2011 281
39. K. Mikami, S. Fustero, M. Sánchez-Roselló, J.L. Aceña, V. Soloshonok, and A. Sorochinsky Synthesis 19 2011 3045
40. J.L. Aceña, A.E. Sorochinsky, and V.A. Soloshonok Synthesis 11 2012 1591
41. A.E. Sorochinsky, and V.A. Soloshonok J. Fluorine Chem. 131 2010 127
42. V.P. Kukhar, A.E. Sorochinsky, and V.A. Soloshonok Future Med. Chem. 1 2009 793
43. C.H. Yun, K.E. Mengwasser, A.V. Toms, M.S. Woo, H. Greulich, K.K. Wong, M. Meyerson, and M.J. Eck Proc. Natl. Acad. Sci. U.S.A. 105 2008 2070
44. R.A. Ward, M.J. Anderton, S. Ashton, P.A. Bethel, M. Box, S. Butterworth, N. Colclough, C.G. Chorley, C. Chuaqui, D.A. Cross, L.A. Dakin, J.É. Debreczeni, C. Eberlein, M.R. Finlay, G.B. Hill, M. Grist, T.C. Klinowska, C. Lane, S. Martin, J.P. Orme, P. Smith, F. Wang, and M.J. Waring J. Med. Chem. 56 2013 7025
45. H. Xie, L. Lin, L. Tong, Y. Jiang, M. Zheng, Z. Chen, X. Jiang, X. Zhang, X. Ren, W. Qu, Y. Yang, H. Wan, Y. Chen, J. Zuo, H. Jiang, M. Geng, and J. Ding PLoS One 6 2011 e21487