Optimization of N-benzyl-benzoxazol-2-ones as receptor antagonists of macrophage migration inhibitory factor (MIF)

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 19, 2010, Pages 5811-5814

  Hare, Alissa A ^a   Leng, Lin ^b   Gandavadi, Sunilkumar ^a   Du, Xin ^b   Cournia, Zoe ^a   Bucala, Richard ^b   Jorgensen, William L ^a  

^a YALE UNIVERSITY   (United States)

^b YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Cytokine; Inflammatory disease; Inhibitor design; MIF; Protein protein interactions

Indexed keywords

BENZOXAZOLE DERIVATIVE; MACROPHAGE MIGRATION INHIBITION FACTOR; MITOGEN ACTIVATED PROTEIN KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE 3; RECEPTOR BLOCKING AGENT;

ARTICLE; BINDING ASSAY; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME PHOSPHORYLATION; IC 50; PROTEIN PROTEIN INTERACTION; REACTION OPTIMIZATION; SIGNAL TRANSDUCTION;

ANTIGENS, DIFFERENTIATION, B-LYMPHOCYTE; BENZOXAZOLES; BINDING SITES; COMPUTER SIMULATION; FIBROBLASTS; HISTOCOMPATIBILITY ANTIGENS CLASS II; HUMANS; MITOGEN-ACTIVATED PROTEIN KINASE 1; MITOGEN-ACTIVATED PROTEIN KINASE 3; PHOSPHORYLATION; PROTEIN STRUCTURE, TERTIARY; RECEPTORS, IMMUNOLOGIC;

MAMMALIA;

EID: 77957595054     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.07.129     Document Type: Article

References (24)

1. R. Bucala Nature 408 2000 146
2. M. Orita, S. Yamamoto, N. Katayama, and S. Fujita Curr. Pharm. Des. 8 2002 1297
3. E.F. Morand, M. Leech, and J. Bernhagen Nat. Rev. Drug Disc. 5 2006 399
4. L. Leng, C.N. Metz, Y. Fang, J. Xu, S. Donnelly, J. Baugh, T. Delohery, Y. Chen, R.A. Mitchell, and R. Bucala J. Exp. Med. 197 2003 1467
5. X. Shi, L. Leng, T. Wang, W. Wang, X. Du, J. Li, C. McDonald, Z. Chen, J.W. Murphy, E. Lolis, P. Noble, W. Knudson, and R. Bucala Immunity 25 2006 595
6. K.L. Meyer-Siegler, K.A. Iczkowski, L. Leng, R. Bucala, and P.L. Vera J. Immunol. 177 2006 8730
7. G. Fingerle-Rowson, D.R. Kaleswarapu, C. Schlander, N. Kabgani, T. Brocks, N. Reinart, R. Busch, A. Schütz, H. Lue, X. Du, A. Liu, H. Xiong, Y. Chen, A. Nemajerova, M. Hallek, J. Bernhagen, L. Leng, and R. Bucala Mol. Cell Biol. 29 2009 1922
8. P.D. Senter, Y. Al-Abed, C.N. Metz, F. Benigni, R.A. Mitchell, J. Chesney, J. Han, C.G. Gartner, S.D. Nelson, G.J. Todaro, and R. Bucala Proc. Natl. Acad. Sci. U.S.A. 99 2002 144
9. J.B. Lubetsky, M. Swope, C. Dealwis, P. Blake, and E. Lolis Biochemistry 38 1999 7346
10. L.R. McLean, Y. Zhang, H. Li, Y.-M. Choi, Z. Han, R.J. Vaz, and Y. Li Bioorg. Med. Chem. Lett. 20 2010 1821
11. S.L. Stamps, M.C. Fitzgerald, and C.P. Whitman Biochemistry 37 1998 10195
12. T.A. Soares, D.S. Goodsell, R. Ferreira, A.J. Olson, and J.M. Briggs J. Mol. Recognit. 13 2000 146
13. M. Winner, J. Meier, S. Zierow, B.E. Rendon, G.V. Crichlow, R. Riggs, R. Bucala, L. Leng, N. Smith, E. Lolis, J.O. Trent, and R.A. Mitchell Cancer Res. 68 2008 7253
14. R. Bucala, and E. Lolis Drug News Perspect. 18 2005 417
15. Z. Cournia, L. Leng, S. Gandavadi, X. Du, R. Bucala, and W.L. Jorgensen J. Med. Chem. 52 2009 416
16. J. Bernhagen, R.A. Mitchell, T. Calandra, W. Voelter, A. Cerami, and R. Bucala Biochemistry 33 1994 14144
17. glide, version 5.5; Schrödinger, LLC, New York, NY, 2009.
18. R.A. Friesner, R.B. Murphy, M.P. Repasky, L.L. Frye, J.R. Greenwood, T.A. Halgren, P.C. Sanschagrin, and D.T. Mainz J. Med. Chem. 49 2006 6177
19. W.L. Jorgensen, and J. Tirado-Rives J. Comput. Chem. 26 2005 1689
20. W.L. Jorgensen, and J. Tirado-Rives Proc. Natl. Acad. Sci. U.S.A. 102 2005 6665
21. W.L. Jorgensen Acc. Chem. Res. 42 2009 724 733
22. Ouertatani-Sakouhi, H.; El-Turk, F.; Fauvet, B.; Cho, M.-K.; Karpinar, D. P.; Le Roy, D.; Dewor, M.; Roger, T.; Bernhagen, J.; Calandra, T.; Zweckstetter, M.; Lashuel, H. A. J. Biol. Chem. In press, M110.113951. doi:10.1074/jbc.M110.113951.
23. G.V. Crichlow, J.B. Lubetsky, L. Leng, R. Bucala, and E.J. Lolis Biochemistry 48 2009 132
24. M. Ohori Drug News Perspect. 21 2008 245