Synthesis and structure-activity relationship of 6-arylureido-3-pyrrol-2- ylmethylideneindolin-2-one derivatives as potent receptor tyrosine kinase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 13, 2010, Pages 4674-4686

  Khanwelkar, Rahul R ^a   Chen, Grace Shiahuy ^b   Wang, Hsiao Chun ^a   Yu, Chao Wu ^a   Huang, Chiung Hua ^a   Lee, On ^c   Chen, Chih Hung ^c   Hwang, Chrong Shiong ^c   Ko, Ching Huai ^c   Chou, Nien Tzu ^c   Lin, Mai Wei ^c   Wang, Ling Mei ^c   Chen, Yen Chun ^c,d   Hseu, Tzong Hsiung ^d   Chang, Chia Ni ^c   Hsu, Hui Chun ^c   Lin, Hui Chi ^c   Shih, Ying Chu ^c   Chou, Shuen Hsiang ^c   Tseng, Hsiang Wen ^c   Liu, Chih Peng ^c   Tu, Chia Mu ^c   Hu, Tsan Lin ^c   Tsai, Yuan Jang ^c   Chern, Ji Wang ^a,e   more..

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b PROVIDENCE UNIVERSITY   (Taiwan)

^c INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE   (Taiwan)

^d NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^e NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

Anticancer; Inhibitor; Platelet derived growth factor receptor; Receptor tyrosine kinase; Structure activity relationship; Vascular endothelial growth factor receptor

Indexed keywords

1 (3,4 DIMETHOXYPHENYL) 3 [2 OXO 3 (1H PYRROL 2 YLMETHYLENE) 2,3 DIHYDRO 1H INDOL 6 YL] UREA; 1 (4 CHLOROPHENYL) 3 [2 OXO 3 (1H PYRROL 2 YLMETHYLENE) 2,3 DIHYDRO 1H INDOL 6 YL] UREA; 1 (4 METHOXYPHENYL) 3 [2 OXO 3 (1H PYRROL 2 YLMETHYLENE) 2,3 DIHYDRO 1H INDOL 6 YL] UREA; 1 [2 OXO 3 (1H PYRROL 2 YLMETHYLENE) 2,3 DIHYDRO 1H INDOL 6 YL] 3 (4 PHENOXYPHENYL) UREA; 1 [2 OXO 3 (1H PYRROL 2 YLMETHYLENE) 2,3 DIHYDRO 1H INDOL 6 YL] 3 (4 TOLYL) UREA; 1 [2 OXO 3 (1H PYRROL 2 YLMETHYLENE) 2,3 DIHYDRO 1H INDOL 6 YL] 3 PHENYL UREA; 1 [3 (3,5 DIMETHYL 4 PHENYL 1H PYRROL 2 YLMETHYLENE) 2 OXO 2,3 DIHYDRO 1H INDOL 6 YL] 3 (4 METHOXYPHENYL) UREA; 1 BIPHENYL 4 YL 3 [2 OXO 3 (1H PYRROL 2 YLMETHYLENE) 2,3 DIHYDRO 1H INDOL 6 YL] UREA; 1 NAPHTHALEN 2 YL 3 [2 OXO 3 (1H PYRROL 2 YLMETHYLENE) 2,3 DIHYDRO 1H INDOL 6 YL] UREA; 2,4 DIMETHYL 5 [2 OXO 6 (3 4 TOLYLUREIDO) 1,2 DIHYDROINDOL 3 YLIDENE METHYL] 1H PYRROLE 3 CARBOXYLIC ACID; 2,4 DIMETHYL 5 [2 OXO 6 (3 PHENYLUREIDO) 1,2 DIHYDROINDOL 3 YLIDENE METHYL] 1H PYRROLE 3 CARBOXYLIC ACID; 3 [5 (6 (3 (4 METHOXYPHENYL) UREIDO) 2 OXO 1,2 DIHYDROINDOL 3 YLIDENE METHYL) 2,4 DIMETHYL 1H PYRROL 3 YL] PROPIONIC ACID; 4 METHYL 5 [2 OXO 6 (3 PHENYLUREIDO) 1,2 DIHYDROINDOL 3 YLIDENEMETHYL] 1H PYRROLE 2 CARBOXYLIC ACID; 5 [6 (3 (4 CHLOROPHENYL) UREIDO) 2 OXO 1,2 DIHYDROINDOL 3 YLIDENE METHYL] 2,4 DIMETHYL 1H PYRROLE 3 CARBOXYLIC ACID; 5 [6 (3 (4 CHLOROPHENYL) UREIDO) 2 OXO 1,2 DIHYDROINDOL 3 YLIDENE METHYL] 4 METHYL 1H PYRROLE 2 CARBOXYLIC ACID; 5 [6 (3 (4 METHOXYPHENYL) UREIDO) 2 OXO 1,2 DIHYDROINDOL 3 YLIDENE METHYL] 1H PYRROLE 2 CARBOXYLIC ACID; 5 [6 (3 (4 METHOXYPHENYL) UREIDO) 2 OXO 1,2 DIHYDROINDOL 3 YLIDENE METHYL] 2,4 DIMETHYL 1H PYRROLE 3 CARBOXYLIC ACID; 5 [6 (3 (4 METHOXYPHENYL) UREIDO) 2 OXO 1,2 DIHYDROINDOL 3 YLIDENE METHYL] 4 METHYL 1H PYRROLE 3 CARBOXYLIC ACID; 5 [6 (3 (4 METHOXYPHENYL) URIDO) 2 OXO 1,2 DIHYDRO INDOL 3 YLIDENE METHYL] THIOPHEN 2 CARBOXYLIC ACID; 6 ARYLUREIDO 3 PYRROL 2 YLMETHYLIDENEINDOLIN 2 ONE DERIVATIVE; [2,4 DIMETHYL 5 (2 OXO 6 (3 PHENYLUREIDO) 1,2 DIHYDROINDOL 3 YLIDENE METHYL) 1H PYRROL 3 YL] ACETIC ACID; [5 (6 (3 (4 METHOXYPHENYL) UREIDO) 2 OXO 1,2 DIHYDROINDOL 3 YLIDENE METHYL) 2,4 DIMETHYL 1H PYRROL 3 YL] ACETIC ACID; AURORA A KINASE; OXINDOLE; PLATELET DERIVED GROWTH FACTOR RECEPTOR; PROTEIN TYROSINE KINASE INHIBITOR; UNCLASSIFIED DRUG; UREIDOINDOLIN 2 ONE DERIVATIVE; VASCULOTROPIN RECEPTOR;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CANCER INHIBITION; CELL FUNCTION; CONTROLLED STUDY; CYTOTOXICITY; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG HALF LIFE; DRUG IDENTIFICATION; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; FEMALE; LEUKEMIA CELL; MALE; MAXIMUM PLASMA CONCENTRATION; MOUSE; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; TIME TO MAXIMUM PLASMA CONCENTRATION; TUMOR XENOGRAFT; WESTERN BLOTTING;

ANIMALS; BINDING SITES; CELL LINE, TUMOR; COMPUTER SIMULATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDOLES; LEUKEMIA, MYELOID; MICE; PROTEIN KINASE INHIBITORS; PROTEIN-SERINE-THREONINE KINASES; PYRROLES; RECEPTOR, EPIDERMAL GROWTH FACTOR; RECEPTORS, PLATELET-DERIVED GROWTH FACTOR; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSPLANTATION, HETEROLOGOUS; UREA;

MUS MUSCULUS;

EID: 77954215388     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.05.021     Document Type: Article

References (44)

1. W. Risau Nature 386 1997 671
2. D.A. Walsh, and L. Haywood Curr. Opin. Invest. Drugs 2 2001 1054
3. J. Spranger, and A.F. Pfeiffer Exp. Clin. Endocrinol. Diabetes 109 2001 S438
4. J. McLaren, A. Prentice, D.S. Charnock-Jones, S.A. Millican, K.H. Muller, A.M. Sharkey, and S.K. Smith J. Clin. Invest. 98 1996 482
5. N. Ferrara, and K. Alitalo Nat. Med. 5 1999 1359
6. L.P. Aiello, R.L. Avery, P.G. Arrigg, B.A. Keyt, H.D. Jampel, S.T. Shah, L.R. Pasquale, H. Thieme, M.A. Iwamoto, and J.E. Park N. Eng. J. Med. 331 1994 1480
7. J. Folkman J. Natl. Cancer Inst. 82 1990 4
8. L.A. Liotta, P.S. Steeg, and W.G. Stetler-Stevenson Cell 64 1991 327
9. A. Bardelli, D.W. Parsons, N. Silliman, J. Ptak, S. Szabo, S. Saha, S. Markowitz, J.K.V. Willson, G. Parmigiani, K.W. Kinzler, B. Vogelstein, and V.E. Velculescu Science 300 2003 949
10. G.D. Yancopoulos, S. Davis, N.W. Gale, J.S. Rudge, S.J. Wiegand, and J. Holash Nature 407 2000 242
11. D. Wang, H.-J.S. Huang, A. Kazlauskas, and W.K. Cavenee Cancer Res. 59 1999 1464
12. E.Y. Lin, A.V. Nguyen, R.G. Russell, and J.W. Pollard J. Exp. Med. 193 2001 727
13. D.L. Stirewalt, and J.P. Radich Nat. Rev. Cancer 3 2003 650
14. M.L. Lux, B.P. Rubin, T.L. Biase, C.-J. Chen, T. Maclure, G. Demetri, S. Xiao, S. Singer, C.D.M. Fletcher, and J.A. Fletcher Am. J. Pathol. 156 2002 791
15. A. Gschwind, O.M. Fisher, and A. Ullrich Nat. Rev. Cancer 4 2004 361
16. W.D. Fox, B. Higgins, K.M. Maiese, M. Drobnjak, C. Cordon-Cardo, H.I. Scher, and D.B. Agus Clin. Cancer Res. 8 2001 3226
17. F. Kabbinavar, H.I. Hurwitz, L. Fehrenbacher, N.J. Meropol, W.F. Novotny, G. Lieberman, S. Griffing, E. Bergsland, and J. Phase II Clin. Oncol. 21 2003 60
18. A. Stopeck, M. Sheldon, M. Vahedian, G. Cropp, R. Gosalia, and A. Hannah Clin. Cancer Res. 8 2002 2798
19. J.M. Wood, G. Bold, E. Buchdunger, R. Cozens, S. Ferrari, J. Frei, F. Hofmann, J. Mestan, H. Mett, T. O'Reilly, E. Persohn, J. Rösel, C. Schnell, D. Stover, A. Theuer, H. Towbin, F. Wenger, K. Woods-Cook, A. Menrad, G. Siemeister, M. Schirner, K.-H. Thierauch, M.R. Schneider, J. Drevs, G. Martiny-Baron, F. Totzke, and D. Marmé Cancer Res. 60 2000 2178
20. J. Beebe, J. Jani, E. Knauth, P. Goodwin, C. Higdon, A. Rossi, E. Emerson, M. Finkelstein, E. Floyd, S. Harriman, J. Atherton, S. Hillerman, C. Soderstrom, K. Kou, T. Gant, M. Noe, B. Foster, F. Rastinejad, M. Marx, T. Schaeffer, P. Whalen, and W. Roberts Cancer Res. 63 2003 7301
21. A. Abdollahi, K.E. Lipson, X. Han, R. Krempien, T. Trinh, K.J. Weber, P. Hahnfeldt, L. Hlatky, J. Debus, A.R. Howlett, and P.E. Huber Cancer Res. 63 2003 3755
22. F. Ciardiello, R. Caputo, V. Damiano, R. Caputo, T. Troiani, D. Vitagliano, F. Carlomagno, B.M. Veneziani, G. Fontanini, A.R. Bianco, and G. Tortora Clin. Cancer Res. 9 2003 1546
23. P. Carmeliet Nat. Med. 9 2003 653
24. J. Adams, P. Huang, and D. Patrick Curr. Opin. Chem. Biol. 6 2002 486
25. C.L. Arteaga Clin. Cancer Res. 9 2003 1231
26. G. Marcucci, D. Perrotti, and M.A. Caligiuri Clin. Cancer Res. 9 2003 1248
27. K. Pietras, and D. Hanahan J. Clin. Oncol. 23 2005 939
28. M. Atkins, C.A. Jones, and P. Kirkpatrick Nat. Rev. Drug Disc. 5 2006 279
29. R. Ng, and E.X. Chen Curr. Clin. Pharmacol. 1 2006 223
30. M.H. Nelson, and C.R. Dolder Ann. Pharmacother. 40 2006 261
31. A.M. Thompson, A.M. Delaney, J.M. Hamby, M.C. Schroeder, T.A. Spoon, S.M. Crean, H.D.H. Showalter, and W.A. Denny J. Med. Chem. 48 2005 4628
32. C.J. Dimitroff, W. Klohs, A. Sharma, P. Pera, D. Driscoll, J. Veith, R. Steinkampf, M. Schroeder, S. Klutchko, A. Sumlin, B. Henderson, T.J. Dougherty, and R.J. Bernacki Invest. New Drugs 17 1999 121
33. J. Dinges, K.L. Ashworth, I. Akritopoulou-Zanze, L.D. Arnold, S.A. Baumeister, P.F. Bousquet, G.A. Cunha, S.K. Davidsen, S.W. Djuric, V.J. Gracias, M.R. Michaelides, P. Rafferty, T.J. Sowin, K.D. Stewart, Z. Xia, and H.Q. Zhang Bioorg. Med. Chem. Lett. 16 2006 4266
34. Y. Dai, K. Hartandi, Z. Ji, A.A. Ahmed, D.H. Albert, J.L. Bauch, J.J. Bouska, P.F. Bousquet, G.A. Cunha, K.B. Glaser, C.M. Harris, D. Hickman, J. Guo, J. Li, P.A. Marcotte, K.C. Marsh, M.D. Moskey, R.L. Martin, A.M. Olson, D.J. Osterling, L.J. Pease, N.B. Soni, K.D. Stewart, V.S. Stoll, P. Tapang, D.R. Reuter, S.K. Davidsen, and M.R. Michaelides J. Med. Chem. 50 2007 1584
35. Y. Dai, Y. Guo, R.R. Frey, Z. Ji, M.L. Curtin, A.A. Ahmed, D.H. Albert, L. Arnold, S.S. Arries, T. Barlozzari, J.L. Bauch, J.J. Bouska, P.F. Bousquet, G.A. Cunha, K.B. Glaser, J. Guo, J. Li, P.A. Marcotte, K.C. Marsh, M.D. Moskey, L.J. Pease, K.D. Stewart, V.S. Stoll, P. Tapang, N. Wishart, S.K. Davidsen, and M.R. Michaelides J. Med. Chem. 48 2005 6066
36. K. Kubo, T. Shimizu, S. Ohyama, H. Murooka, A. Iwai, K. Nakamura, K. Hasegawa, Y. Kobayashi, N. Takahashi, K. Takahashi, S. Kato, T. Izawa, and T. Isoe J. Med. Chem. 48 2005 1359
37. L. Sun, C. Liang, S. Shirazian, Y. Zhou, T. Miller, J. Cui, J.Y. Fukuda, J.Y. Chu, A. Nematalla, X. Wang, H. Chen, A. Sistla, T.C. Luu, F. Tang, J. Wei, and C. Tang J. Med. Chem. 46 2003 1116
38. L. Sun, N. Tran, T. Tang, H. App, P. Hirth, G. McMahon, and C. Tang J. Med. Chem. 41 1998 2588
39. A.D. Laird, P. Vajkoczy, L.K. Shawver, A. Thurnher, C. Liang, M. Mohammadi, J. Schlessinger, A. Ullrich, S.R. Hubbard, R.A. Blake, A.T. Fong, L.M. Strawn, L. Sun, C. Tang, R. Hawtin, F. Tang, N. Shenoy, K.P. Hirth, G. McMahon, and J.M. Cherrington Cancer Res. 60 2000 4152
40. Wan, Y.; Mi, Y.; Fan, Y.; Cheng, D.; Liu, Y.; Gray, N. S.; Albaugh, P. WO Patent 052936 A2, 2006.
41. Y.L. Leu, C.S. Chen, Y.J. Wu, and J.-W. Chern J. Med. Chem. 51 2008 1740
42. J.-W. Chern, Y.L. Leu, S.S. Wang, R. Jou, C.F. Lee, P.C. Tsou, S.C. Hsu, Y.C. Liaw, and H.M. Lin J. Med. Chem. 40 1997 2276
43. T. Nakashima, and I. Suzuki Chem. Pharm. Bull. 17 1969 2293
44. Michael, B. C.; Gray, M. K. US Patent 5,252,536, 1993.