Discovery of novel 4-(2-fluorophenoxy)quinoline derivatives bearing 4-oxo-1,4-dihydrocinnoline-3-carboxamide moiety as c-Met kinase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 11, 2013, Pages 2843-2855

  Li, Sai ^a   Zhao, Yanfang ^a   Wang, Kewen ^a   Gao, Yali ^a   Han, Jianming ^a   Cui, Bingbing ^a   Gong, Ping ^a  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

4 (2 Fluorophenoxy)quinoline derivatives; 4 Oxo 1,4 dihydrocinnoline 3 carboxamide; c Met; Receptor tyrosine kinase

Indexed keywords

1 (2 BROMOPHENYL) N [3 FLUORO 4 [6 METHOXY 7 [3 (4 METHYLPIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; 1 (2 CHLOROPHENYL) N [3 FLUORO 4 [6 METHOXY 7 [3 (PIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; 1 (2,4 DICHLOROPHENYL) N [3 FLUORO 4 [6 METHOXY 7 [3 (PIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; 1 (2,4 DIMETHYPHENYL) N [3 FLUORO 4 [6 METHOXY 7 [3 (PIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; 1 (2,5 DIMETHYLPHENYL) N [3 FLUORO 4 [6 METHOXY 7 [3 (PYRROLIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; 1 (2,6 DICHLOROPHENY) N [3 FLUORO 4 [6 METHOXY 7 [3 (PIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; 1 (2,6 DICHLOROPHENYL) N [3 FLUORO 4 [6 METHOXY 7 [3 (4 METHYLPIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; 1 (2,6 DICHLOROPHENYL) N [3 FLUORO 4 [6 METHOXY 7 [3 (PIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; 1 (3,4 DIFLUOROPHENYL) N [3 FLUORO 4 [6 METHOXY 7 [3 (PIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; 1 (4 BROMOPHENYL) N [3 FLUORO 4 [6 METHOXY 7 [3 (PIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; 1 (4 CHLOROPHENYL) N [3 FLUORO 4 [6 METHOXY 7 [3 (PIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; 1 [2 CHLORO 5 (TRIFLUOROMETHYL)PHENYL] N [3 FLUORO 4 [6 METHOXY 7 [3 (4 METHYLPIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; 1 [4 CHLORO 3 (TRIFLUOROMETHYL)PHENYL] N [3 FLUORO 4 [6 METHOXY 7 [3 (4 METHYLPIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; 4 (2 FLUOROPHENOXY)QUINOLINE DERIVATIVE; 4 OXO 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE DERIVATIVE; ANTINEOPLASTIC AGENT; ENZYME INHIBITOR; FORETINIB; N [3 FLUORO 4 [6 METHOXY 7 [3 (4 METHYLPIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1 (2 FLUOROPHENYL) 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; N [3 FLUORO 4 [6 METHOXY 7 [3 (4 METHYLPIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1 (4 FLUOROPHENYL) 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; N [3 FLUORO 4 [6 METHOXY 7 [3 (4 METHYLPIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1 4 TOLYL 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; N [3 FLUORO 4 [6 METHOXY 7 [3 (4 METHYLPIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1 [3 (TRIFLUOROMETHYL)PHENYL] 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; N [3 FLUORO 4 [6 METHOXY 7 [3 (PIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1 (3 FLUOROPHENYL) 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; N [3 FLUORO 4 [6 METHOXY 7 [3 (PIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1 [2 (TRIFLUOROMETHYL)PHENYL] 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; N [3 FLUORO 4 [6 METHOXY 7 [3 (PIPERIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1 [3 (TRIFLUOROMETHYL)PHENYL] 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; N [3 FLUORO 4 [6 METHOXY 7 [3 (PYRROLIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1 [2 (TRIFLUOROMETHYL)PHENYL] 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; N [3 FLUORO 4 [6 METHOXY 7 [3 (PYRROLIDIN 1 YL)PROPOXY]QUINOLIN 4 YLOXY]PHENYL] 4 OXO 1 [3 (TRIFLUOROMETHYL)PHENYL] 1,4 DIHYDROCINNOLINE 3 CARBOXAMIDE; PROTEIN TYROSINE KINASE INHIBITOR; SCATTER FACTOR RECEPTOR; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION;

ANILIDES; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR DOCKING SIMULATION; PROTEIN KINASE INHIBITORS; PROTO-ONCOGENE PROTEINS C-MET; QUINOLINES; SPECTROMETRY, FLUORESCENCE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84877823163     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.04.013     Document Type: Article

References (49)

1. P. Longati, P.M. Comoglio, and A. Bardelli Curr. Drug Targets 2 2001 41
2. G. Maulik, A. Shrikhande, T. Kijima, P.C. Ma, P.T. Morrison, and R. Salgi Cytokine Growth Factor Rev. 13 2002 41
3. R. Haddad, K.E. Lipson, and C.P. Webb Anticancer Res. 21 2001 4243
4. K. Matsumoto, K. Date, H. Shimura, and T. Nakamura Jpn. J. Cancer Res. 87 1996 702
5. C. Birchmeier, W. Birchmeier, E. Gherardi, and G.F. Vande Woude Nat. Rev. Mol. Cell Biol. 4 2003 915
6. S. Corso, P.M. Comoglio, and S. Giordano Trends Mol. Med. 11 2005 284
7. M. Jeffers, S. Rong, and G.F. Vande Woude Mol. Cell. Biol. 16 1996 1115
8. I. Dussault, P. Kaplan-Lefko, T. Jun, A. Coxon, and T.L. Burgess Drugs Future 31 2006 819
9. P.C. Ma, G. Maulik, J. Christensen, and R. Salgia Cancer Metastasis Rev. 22 2003 309
10. D.N. D'Angelo, F.S. Bellon, K.S. Booker, Y. Cheng, A. Coxon, C. Dominguez, I. Fellows, D. Hoffman, R. Hungate, P. Kaplan-Lefko, P.M. Lee, C. Li, L. Liu, E. Rainbeau, J.P. Reider, K. Rex, A. Siegmund, Y. Sun, S.A. Tasker, N. Xi, S. Xu, Y. Yang, Y. Zhang, L.T. Burgess, I. Dussault, and T.S. Kim J. Med. Chem. 51 2008 5766
11. B. Cao, Y. Su, M. Oskarsson, P. Zhao, E.J. Kort, R.J. Fisher, L.M. Wang, and G.F.V. Woude Proc. Natl. Acad. Sci. U.S.A. 98 2001 7443
12. T. Burgess, A. Coxon, S. Meyer, J. Sun, K. Rex, T. Tsuruda, Q. Chen, S.Y. Ho, L. Li, S. Kaufman, K. McDorman, R.C. Cattley, J. Sun, G. Elliot, K. Zhang, X. Feng, X.C. Jia, L. Green, R. Radinsky, and R. Kendall Cancer Res. 66 2006 1721
13. K.J. Kim, L. Wang, Y.C. Su, G.Y. Gillespie, A. Salhotra, B. Lal, and J. Laterra Clin. Cancer Res. 12 2006 1292
14. T. Martens, N.O. Schmidt, C. Eckerich, R. Fillbrandt, M. Merchant, R. Schwall, M. Westphal, and K. Lamszus Clin. Cancer Res. 12 2006 6144
15. K. Date, K. Matsumoto, H. Shimura, M. Tanaka, and T. Nakamura FEBS Lett. 420 1997 1
16. D. Tomioka, N. Maehara, K. Kuba, K. Mizumoto, M. Tanaka, K. Matsumoto, and T. Nakamura Cancer Res. 61 2001 7518
17. M.A. Brochmann, A. Papadimitriou, M. Brandt, R. Fillbrandt, M. Westphal, and K. Lamszus Clin. Cancer Res. 9 2003 4578
18. P. Michieli, M. Mazzone, C. Basilico, S. Cavassa, A. Sottile, L. Naldini, and P.M. Comoglio Cancer Res. 6 2004 61
19. M. Kong-Beltran, J. Stamos, and D. Wickramasinghe Cancer Cell 6 2004 75
20. R. Abounader, S. Ranganathan, B. Lal, K. Fielding, A. Book, H. Diez, P. Burger, and J. Laterra J. Natl. Cancer Inst. 91 1999 1548
21. J. Porter Expert Opin. Ther. Pat. 20 2010 159
22. M. Mannion, S. Raeppel, S. Claridge, S. Claridge, N. Zhou, O. Saavedra, L. Isakovic, L. Zhan, F. Gaudette, F. Raeppel, R. Déziel, N. Beaulieu, H. Nguyen, I. Chute, C. Beaulieu, I. Dupont, M.F. Robert, S. Lefebvre, M. Dubay, J. Rahil, J. Wang, H. Ste-Croix, A.R. Macleod, M.J. Besterman, and A. Vaisburg Bioorg. Med. Chem. Lett. 19 2009 6552
23. T. Nakagawa, O. Tohyama, A. Yamaguchi, T. Matsushima, K. Takahashi, S. Funasaka, S. Shirotori, M. Asada, and H. Obaishi Cancer Sci. 101 2010 210
24. O. Saavedra, S. Claridge, L. Zhan, F. Raeppel, M.C. Granger, S. Raeppel, M. Mannion, F. Gaudette, N. Zhou, L. Isakovic, N. Bernstein, R. Déziel, H. Nguyen, B. Normand, C. Beaulieu, I. Dupont, J. Wang, R.A. Macleod, M.J. Besterman, and A. Vaisburg Bioorg. Med. Chem. Lett. 19 2009 6836
25. Z.W. Cai, D. Wei, M.G. Schroeder, A.M.L. Cornelius, K. Kim, X.T. Chen, J.R. Schmidt, K.D. Williams, S.J. Tokarski, Y. An, S.J. Sack, V. Manne, A. Kamath, Y. Zhang, P. Marathe, T.J. Hunt, J.L. Lombardo, J. Fargnoli, and M.R. Borzilleri Bioorg. Med. Chem. Lett. 18 2008 3224
26. J. Caballero, M. Quiliano, H.J. Alzate-Morales, M. Zimic, and E. Deharo J. Comput. Aided Mol. Des. 25 2011 349
27. Q. Sun, C. Ng, R.G. Guy, and J. Sivaraman FEBS Lett. 585 2011 281
28. L.T. Underiner, T. Herbertz, and J.S. Miknyoczki Anticancer Agent Med. 10 2010 7
29. F.M. Yakes, J. Chen, J. Tan, K. Yamaguchi, Y.C. Shi, P.W. Yu, F. Qian, F. Chu, F. Bentzien, B. Cancilla, J. Orf, A. You, A.D. Laird, S. Engst, L. Lee, J. Lesch, Y.C. Chou, and A.H. Joly Mol. Cancer Ther. 10 2011 2298
30. Kollmannsberger, C. K.; Hurwitz, H.; Vlahovic, G.; Maroun, C.; Dumouchel, J.; Reid, G.; Martell, R.; Shapiro, G. The ASCO Annual Meeting, 2009, Abstract, e14525.
31. G.M. Schroeder, Y.M. An, Z.W. Cai, X.T. Chen, C. Clark, L.A.M. Cornelius, J. Dai, J. Gullo-Brown, A. Gupta, B. Henley, J.T. Hunt, R. Jeyaseelan, A. Kamath, K. Kim, J. Lippy, L.J. Lombardo, V. Manne, S. Oppenheimer, J.S. Sack, R.J. Schmidt, G.X. Shen, K. Stefanski, J.S. Tokarski, G.L. Trainor, B.S. Wautlet, D. Wei, D.K. Williams, Y.R. Zhang, Y.P. Zhang, J. Fargnoli, and R.M. Borzilleri J. Med. Chem. 52 2009 1251
32. M. Mannion, S. Raeppel, S. Claridge, N. Zhou, O. Saavedra, L. Isakovic, L. Zhan, F. Gaudette, F. Raeppel, R. Déziel, N. Beaulieu, H. Nguyen, I. Chute, C. Beaulieu, I. Dupont, M.F. Robert, S. Lefebvre, M. Dubay, J. Rahil, J. Wang, H. Ste-Croix, A.R. Macleod, J.M. Beaterman, and A. Vaisburg Bioorg. Med. Chem. Lett. 19 2009 6552
33. S.F. Bellon, P. Kaplan-Lefko, Y.J. Yang, Y.H. Zhang, J. Moriguchi, K. Rex, C.W. Johnson, P.E. Rose, A.M. Long, A.B. O'Connor, Y. Gu, A. Coxon, T.S. Kim, A. Tasker, T.L. Burgess, and I. Dussault J. Biol. Chem. 283 2008 2675
34. T.L. Graybill, R.E. Dolle, I.K. Osifo, S.J. Schmidt, J.S. Gregory, A.L. Harris, and M.S. Miller Bioorg. Med. Chem. Lett. 5 1995 387
35. Muthuppla, N. M.; Margal, S.; Sukeerthi, K.; Khairatkar, J. N.; Karnik, P. WO2009053799-A1.
36. Balasubramanian, G.; Rajagopal, S.; Rathinasamy, S.; Kilambi, N.; Rajendran, P.; Narayanan, S. WO2010073078-A2.
37. M. Wilcox, R.W. Viola, K.W. Johnson, A.P. Billington, B.K. Carpenter, J.A. McCray, A.P. Guzikowski, and G.P. Hess J. Org. Chem. 55 1990 1585
38. J. Tois, M. Vahermo, and A. Koskinen Tetrahedron Lett. 46 2005 735
39. D.Y. Zhang, J. Ai, Z.J. Liang, C.P. Li, X. Peng, Y.C. Ji, H.L. Jiang, M.Y. Geng, C. Luo, and H. Liu Bioorg. Med. Chem. 20 2012 5169
40. M.H. Norman, L. Liu, M. Lee, N. Xi, I. Fellows, N.D. D'Angelo, C. Dominguez, K. Rex, S.F. Bellon, T.S. Kim, and I. Dussault J. Med. Chem. 55 2012 1858
41. D.J. Hogenkamp, T.B.C. Johnstone, J.C. Huang, W.Y. Li, M. Tran, E.R. Whittemore, R.E. Bagnera, and K.W. Gee J. Med. Chem. 50 2007 3369
42. D.E. Ames, O.T. Leung, and A.G. Singh Synthesis 1 1983 52
43. Muthupplaniappan, M.; Margal, S.; Sukeerthi, K.; Khair, N.; Karnik, P. A.; Glenmark, P.; Switz, S. A. WO2009053799-A1.
44. L.B. Liu, A. Siegmund, N. Xi, P. Kaplan-Lefko, K. Rex, A. Chen, J. Lin, J. Moriguchi, L. Berry, L.Y. Huang, Y. Teffera, Y.J. Yang, Y.H. Zhang, S.F. Bellon, M. Lee, R. Shimanovich, A. Bak, C. Dominguez, M.H. Norman, J.C. Harmange, I. Dussault, and T.S. Kim J. Med. Chem. 51 2008 3688
45. M.L. Peach, N. Tan, N. Tan, S.J. Choyke, A. Giubellino, G. Athauda, T.R. Burke, M.C. Nicklaus, and D.P. Bottaro J. Med. Chem. 52 2009 943
46. Z. Zhang, J.C. Lee, V. Olivas, V. Au, T. LaFramboise, M. Abdel-Rahman, X. Wang, A.D. Levine, J.K. Rho, Y.J. Choi, C.M. Choi, S.W. Kim, S.J. Jang, Y.S. Park, W.S. Kim, D.H. Lee, J.S. Lee, V.A. Miller, M. Arcila, M. Ladanyi, P. Moonsamy, C. Sawyers, T.J. Boggon, P.C. Ma, C. Costa, M. Taron, R. Rosell, B. Halmos, and T.G. Bivona Nat. Genet. 44 2012 852
47. R. Tiedt, E. Degenkolbe, P. Furet, B.A. Appleton, S. Wagner, J. Schoepfer, E. Buck, D.A. Ruddy, J.E. Monahan, M.D. Jones, J. Blank, D. Haasen, P. Drueckes, M. Wartmann, C. McCarthy, W.R. Sellers, and F. Hofmann Cancer Res. 71 2011 5255
48. N. Takayuki, T. Osamu, Y. Atsumi, M. Tomohiro, T. Keiko, F. Setsuo, S. Shuji, A. Makoto, and O. Hiroshi Cancer Sci. 101 2010 210
49. L.U. Ted, H. Torsten, and J.M. Sheila Anticancer Agent Med. 10 2010 7