Design, synthesis, and evaluation of quinazoline T cell proliferation inhibitors

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 17, 2010, Pages 6404-6413

  Sagiv Barfi, Idit ^a   Weiss, Ester ^a   Levitzki, Alexander ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

Proliferation; Quinazoline; T cells

Indexed keywords

(2 CHLORO QUINAZOLIN 4 YL) 4 TOLYL AMINE; 1 4 TOLYL [2 (3,4,5 TRIMETHOXY PHENYL)QUINAZOLIN 4 YL]AMINE; 1 MESYLATE: 3 TOLYL [2 (3,4,5 TRIMETHOXY PHENYL)QUINAZOLIN 4 YL]AMINE METHANESULFONIC SALT; 1:5 (4 4 TOLYLAMINO QUINAZOLIN 2 YL)BENZENE 1,2,3 TRIOL; 2,4 DICHLOROQUINAZOLINE; ANTIMITOTIC AGENT; INTERLEUKIN 2; N 4 TOLYL 2 (3,4,5 TRIMETHOXYPHENYL)QUINAZOLIN 4 AMINE; QUINAZOLINE DERIVATIVE; S 101; T LYMPHOCYTE RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL PROLIFERATION; CYTOKINE RELEASE; DRUG DESIGN; DRUG EFFECT; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HEMATOPOIETIC CELL; HUMAN; HUMAN CELL; IMMUNOPRECIPITATION; LEUKEMIA CELL LINE; MIXED LYMPHOCYTE REACTION; PERIPHERAL BLOOD MONONUCLEAR CELL; PROTEIN PHOSPHORYLATION; STRUCTURE ACTIVITY RELATION; T LYMPHOCYTE; WESTERN BLOTTING;

ANIMALS; CELL LINE, TUMOR; HUMANS; JURKAT CELLS; LEUKOCYTES, MONONUCLEAR; LYMPHOCYTE ACTIVATION; MICE; NIH 3T3 CELLS; QUINAZOLINES; T-LYMPHOCYTES;

EID: 77955982658     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.07.004     Document Type: Article

References (41)

1. L.M. Chiu, B.M. Domagala, and J.M. Park Prog. Transplant. 14 2004 114
2. A.C. Allison Immunopharmacology 47 2000 63
3. C.K. Ong, P. Lirk, C.H. Tan, and R.A. Seymour Clin. Med. Res. 5 2007 19
4. M. Rollinghoff, A. Starzinski-Powitz, K. Pfizenmaier, and H. Wagner J. Exp. Med. 145 1977 455
5. J.L. Turk Int. Arch. Allergy Appl. Immunol. 24 1964 191
6. A.C. Allison, S.J. Almquist, C.D. Muller, and E.M. Eugui Transplant. Proc. 23 1991 10
7. Amemiya, H.; Itoh, H. Immunosuppressive drugs: developments in anti-rejection therapy; Thomson, A. W., Starzl, T. E., Eds.; Edward Arnold: London, 1994; pp 161-176.
8. R.G. Cohn, A. Mirkovich, B. Dunlap, P. Burton, S.H. Chiu, E. Eugui, and J.P. Caulfield Transplantation 68 1999 411
9. J.S. Dayton, L.A. Turka, C.B. Thompson, and B.S. Mitchell Mol. Pharmacol. 41 1992 671
10. M.L. Herrmann, R. Schleyerbach, and B.J. Kirschbaum Immunopharmacology 47 2000 273
11. M. Waer Transpl. Immunol. 4 1996 181
12. J.J. Curtis, R.G. Luke, and E. Duborsky Lancet 2 1986 477
13. W.H. Herman, D.E. Hircik, and M.S. Simonson Transplantation 1999 67
14. M. Hojo, T. Morimoto, M. Maluccio, T. Asano, K. Morimoto, M. Lagman, T. Shimbo, and M. Suthanthiran Nature 397 1999 530
15. T. Kino, H. Hatanaka, S. Miyata, N. Inamura, M. Nishiyama, T. Yajima, T. Goto, M. Okuhara, M. Kohsaka, and H. Aoki J. Antibiot. (Tokyo) 40 1987 1256
16. J. Liu, J.D. Farmer Jr., W.S. Lane, J. Friedman, I. Weissman, and S.L. Schreiber Cell 66 1991 807
17. J. Gonzalez, T. Harris, G. Childs, and M.B. Prystowsky Blood Cells Mol. Dis. 27 2001 572
18. R.T. Abraham, and G.J. Wiederrecht Annu. Rev. Immunol. 14 1996 483
19. A.W. Thomson Transpl. Immunol. 2 1994 263
20. I.L. Dodge, X.C. Li, and T.B. Strom Transplantation 1999 67
21. A. Levitzki, and E. Mishani Annu. Rev. Biochem. 75 2006 93
22. M.G. Brasca, N. Amboldi, D. Ballinari, A. Cameron, E. Casale, G. Cervi, M. Colombo, F. Colotta, V. Croci, R. D'Alessio, F. Fiorentini, A. Isacchi, C. Mercurio, W. Moretti, A. Panzeri, W. Pastori, P. Pevarello, F. Quartieri, F. Roletto, G. Traquandi, P. Vianello, A. Vulpetti, and M. Ciomei J. Med. Chem. 52 2009 5152
23. L.A. Skelton, M.G. Ormerod, J.C. Titley, and A.L. Jackman Cytometry 33 1998 56
24. D.S. Theti, V. Bavetsias, L.A. Skelton, J. Titley, D. Gibbs, G. Jansen, and A.L. Jackman Cancer Res. 63 2003 3612
25. G.W. Aherne, E. Ward, N. Lawrence, D. Dobinson, S.J. Clarke, H. Musgrove, F. Sutcliffe, T. Stephens, and A.L. Jackman Br. J. Cancer 77 1998 221
26. T.R. Jones, A.H. Calvert, A.L. Jackman, S.J. Brown, M. Jones, and K.R. Harrap Eur. J. Cancer 17 1981 11
27. Nagarathnam, D.; Asgari, D.; Shao, J.; Liu, X.-G.; Khire, U.; Wang, C.; Hart, B.; Boyer, S. PCT/US02/08659, 2002.
28. W.R. Perrault, K. Paul Shephard, L.A. LaPean, M.A. Krook, P.J. Dobrowolski, M.A. Lyster, M.W. McMillan, D.J. Knoechel, G.N. Evenson, W. Watt, and B.A. Pearlman Org. Proc. Res. Dev. 1 1997 106
29. S. Reich-Zeliger, J. Gan, E. Bachar-Lustig, and Y. Reisner J. Immunol. 173 2004 6660
30. D. Yablonski, L.P. Kane, D. Qian, and A. Weiss EMBO J. 17 1998 5647
31. N. Sirisoma, A. Pervin, H. Zhang, S. Jiang, J.A. Willardsen, M.B. Anderson, G. Mather, C.M. Pleiman, S. Kasibhatla, B. Tseng, J. Drewe, and S.X. Cai J. Med. Chem. 52 2009 2341
32. D.J. Baker, C.R. Beddell, J.N. Champness, P.J. Goodford, F.E. Norrington, D.R. Smith, and D.K. Stammers FEBS Lett. 126 1981 49
33. B. Apsel, J.A. Blair, B. Gonzalez, T.M. Nazif, M.E. Feldman, B. Aizenstein, R. Hoffman, R.L. Williams, K.M. Shokat, and Z.A. Knight Nat. Chem. Biol. 4 2008 691
34. L. Wright, X. Barril, B. Dymock, L. Sheridan, A. Surgenor, M. Beswick, M. Drysdale, A. Collier, A. Massey, N. Davies, A. Fink, C. Fromont, W. Aherne, K. Boxall, S. Sharp, P. Workman, and R.E. Hubbard Chem. Biol. 11 2004 775
35. A.S. Kendall Med. Immunol. 2006 14
36. G.H. Cornish, L.V. Sinclair, and A. Doreen Blood 2006 600
37. W. Haussmann Contrib Oncol 55 2000 62
38. J.K. Jackman, D.G. Motto, Q. Sun, M. Tanemoto, C.W. Turck, G.A. Peltz, G.A. Koretzky, and P.R. Findell J. Biol. Chem. 270 1995 7029
39. E.P. Pedro, W. Soujuan, C. Holly, L. Xaiobin, S. David, and A. Arie Biochem. J. 2001 461
40. D. Yablonski, M.R. Kuhne, T. Kadlecek, and A. Weiss Science 281 1998 413
41. O. Boyman, H.P. Hefti, C. Conrad, B.J. Nickoloff, M. Suter, and F.O. Nestle J. Exp. Med 2004 199