Synthesis and activity of novel 5-substituted pyrrolo[2,3-d]pyrimidine analogues as pp60c-Src tyrosine kinase inhibitors

Archiv der Pharmazie

Volumn 341, Issue 2, 2008, Pages 113-120

  Ölgen, Süreyya ^a   Isgör, Yasemin G ^a   Çoban, Tülay ^a  

^a ANKARA UNIVERSITY   (Turkey)

Author keywords

Cancer; Pyrrolopyrimidine derivatives; Schiff bases; Tyrosine kinase pp60 c Src

Indexed keywords

2 AMINO 5 [(BENZYL)IMINO]METHYL 3,7 DIHYDRO 4H PYRROLO[2,3 D]PYRIMIDIN 4 ONE DERIVATIVE; 2 TRITYLAMINO 4 OXO 4,7 DIHYDRO 3H PYRROLO[2,3 D]PYRIMIDINE 5 CARBALDEHYDE; BENZYLAMINE DERIVATIVE; PROTEIN KINASE P60; PROTEIN TYROSINE KINASE INHIBITOR; PYRROLO[2,3 D]PYRIMIDINE DERIVATIVE; REAGENT; SCHIFF BASE; UNCLASSIFIED DRUG; PYRIMIDINE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DETRITYLATION; DRUG ACTIVITY; DRUG INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS; HEART INFARCTION; IC 50; NEOPLASM; NERVE DEGENERATION; OSTEOPOROSIS; POLYMERIZATION; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION; STROKE; SUBSTITUTION REACTION; CHEMISTRY; DRUG ANTAGONISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

PROTO-ONCOGENE PROTEINS PP60(C-SRC); PYRIMIDINES; PYRROLES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 43149124428     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.200700141     Document Type: Article

References (38)

1. A. J. Bridges, Chem. Rev. 2001, 101, 2541-2571.
2. M. Warmuth, R. Damoiseaux, Y. Liu, D. Fabbro, N. Gray, Curr. Pharm. Des. 2003, 9, 2043-2059.
3. J. S. Biscardi, D. A. Tice, S. J. Parsons, Adv. Cancer Res. 1999, 76, 61-119.
4. M. Warmuth, R. Damoiseaux, Y. Liu, D. Fabbro, N. Gray, Curr. Pharm. Des. 2003, 9, 2043-2059.
5. Y.-P. Chong, A. S. Chan, K.-C. Chan, N. A. Williamson, et al., J. Biol. Chem. 2006, 281, 32988-32999.
6. J. H. Hanke, J. P. Gardner, R. L. Dow, P. S. Changelian, et al., J. Biol. Chem. 1996, 271, 695-701.
7. S. B. Noonberg, C. C. Benz, Drugs 2000, 59, 753-767.
8. J. M. Hamby, H. D. H. Showalter, Pharmacol. Ther. 1999, 82, 169-193.
9. L. Widler, J. Green, M. Missbach, M. Susa, E. Altmann, Bioorg. Med. Chem. Lett. 2001, 11, 849-852.
10. A. M. Thompson, G. W. Rewcastle, S. L. Boushelle, B. G. Hartl, et al., J. Med. Chem. 2000, 43, 3134-3147.
11. A. Bennasroune, A. Gardin, D. Aunis, G. Cremel, P. Hubert, Crit. Rev. Oncol. Hematol. 2004, 50, 23-38.
12. S. R. Hubbard, Curr. Opin. Struc. Biol. 2002, 12, 735-741.
13. S. P. Davies, H. Reddy, M. Caivano, P. Cohen, Biochem. J. 2000, 35, 95-105.
14. M. Levitzki, Eur. J. Cancer. 2002, 38, S11-S18.
15. L. F. Hennequin, E. S. E. Stokes, A. P. Thomas, C. Johnstone, et al., J. Med. Chem. 2002, 45, 1300-1312.
16. M. F. Brana, M. Cacho, M. L. Garcia, E. P. Mayoral, et al., J. Med. Chem. 2005, 48, 6843-6854.
17. A. Gangjee, Y. Zeng, J. J. Mc Guire, R. L. Kisliuk, J. Med. Chem. 2005, 48, 5329-5336.
18. A. Gangjee, A. Vidwans, E. Elzein, J. J. Mc Guire, et al., J. Med. Chem. 2001, 44, 1993-2003.
19. A. Gangjee, Y. Zeng, M. Ihnat, L. A. Warnke, et al., Bioorg. Med. Chem. 2005, 13, 5475-5491.
20. A. Gangjee, A. Vidwans, E. Elzein, J. J. Mc Guire, et al., J. Med. Chem. 2001, 44, 1993-2003.
21. P. Traxler, G. Bold, J. Frei, M. Lang, et al., J. Med. Chem. 1997, 40, 3601-3616.
22. C. R. Loomis, R. M. Bell, J. Biol. Chem. 1988, 263, 1682-1692.
23. X. Zhu, J. L. Kim, J. R. Newcomb, P. E. Rose, et al., Structure 1999, 7, 651-661.
24. L. Widler, J. Green, M. Missbach, M. Susa, E. Altmann, Bioorg. Med. Chem. Lett. 2001, 11, 849-852.
25. E. Altmann, M. Missbach, J. Green, M. Susa, et al., Bioorg. Med. Chem. Lett. 2001, 11, 853-856.
26. C. Shih, L. S. Gosset, Heterocycles 1993, 35, 825-841.
27. M. S. Duxbury, H. Ito, M. J. Zinner, S. W. Ashley, E. E. Whang, Clin. Cancer. Res. 2004, 10, 2307-2318.
28. M. T. Migawa, J. M. Hinkley, G. C. Hoops, L. B. Townsend, Synth. Commun. 1996, 26, 3317-3322.
29. R. Dalpozzo, A. De Nino, L. Maiuolo, A. Procopio, et al., Tetrahedron 2001, 57, 4035-4038.
30. G. C. Hoops, L. B. Townsend, G. A. Garcia, Biochemistry 1995, 34, 15381-15387.
31. P. Kutschy, M. Dzurilla, M. Takasugi, M. Török, et al., Tetrahedron 1998, 54, 3549-3566.
32. E. O. M. Orlemans, W. Verboom, M. W. Scheltinga, D. N. Reinhoudt, et al., J. Med. Chem. 1989, 32, 1612-1620.
33. N. Selvakumar, M. K. Khera, B. Y. Reddy, D. Srinivas, et al., Tetrahedron Lett. 2003, 44, 7071-7074.
34. D. Bonifazi, M. Scholl, S. Markus, E. Fayi, A. Luis, Angew. Chem. Int. 2003, 42, 4966-4970.
35. M. E. El-Araby, R. J. Bernacki, G. M. Makara, P. J. Pera, W. K. Anderson, Bioorg. Med. Chem. 2004, 12, 2867-2879.
36. E. Winterfield, Synthesis 1975, 10, 617-630.
37. C. L. Gibson, S. La Rosa, K. Ohta, P. H. Boyle, et al., Tetrahedron 2004, 60, 943-959.
38. V. C. Taylor, C. D. Buckley, M. Douglas, A. J. Cody, et al., J. Biol. Chem. 1999, 274, 11505-11512.