Novel ketal ligands for the glucocorticoid receptor: In vitro and in vivo activity

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 11, 2005, Pages 2926-2931

  Smith, Cameron J ^a   Ali, Amjad ^a   Balkovec, James M ^a   Graham, Donald W ^a   Hammond, Milton L ^a   Patel, Gool F ^a   Rouen, Gregory P ^a   Smith, Scott K ^a   Tata, James R ^a   Einstein, Monica ^a   Ge, Lan ^a   Harris, Georgianna S ^a   Kelly, Theresa M ^a   Mazur, Paul ^a   Thompson, Chris M ^a   Wang, Chuanlin F ^a   Williamson, Joanne M ^a   Miller, Douglas K ^a   Pandit, Shilpa ^a   Santoro, Joseph C ^a   Sitlani, Ayesha ^a   Yamin, Ting Ting D ^a   O'Neill, Edward A ^a   Zaller, Dennis M ^a   Carballo Jane, Ester ^a   Forrest, Michael J ^a   Luell, Silvi ^a   more..

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Dissociation; Glucocorticoid; Inflammation; Transactivation; Transrepression

Indexed keywords

GLUCOCORTICOID RECEPTOR; KETONE DERIVATIVE; PREDNISOLONE;

ARTICLE; CONTROLLED STUDY; EVALUATION; HUMAN; HUMAN CELL; LIGAND BINDING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARTICLE SIZE; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANIMALS; CELLS, CULTURED; HUMANS; LIGANDS; MICE; RECEPTORS, GLUCOCORTICOID;

EID: 21144434807     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.03.027     Document Type: Article

References (36)

1. B.P. Schimmer, and K.L. Parker J.G. Hardman L.E. Limbird A.G. Gilman Goodman and Gilman's The Pharmacological Basis of Therapeutics 10 ed. 2001 McGraw-Hill New York 1649 1677
2. M.J. Coghlan, S.W. Elmore, P.R. Kym, and M.E. Kort Curr. Top. Med. Chem. 3 2003 1617 1635
3. H. Schäcke, W.D. Döcke, and K. Asadullah Pharmacol. Ther. 96 2002 23 43
4. E. Schmid, W. Schmid, M. Jantzen, D. Mayer, B. Jastorff, and G. Schüntz Eur. J. Biochem. 165 1987 499 506
5. J.N. Miner Biochem. Pharmacol. 64 2002 355 361
6. M.J. Coghlan, and M.E. Kort Exp. Opin. Ther. Patents 9 1999 1523 1536
7. M.J. Coghlan, P.R. Kym, S.W. Elmore, A.X. Wang, J.R. Luly, D. Wilcox, M. Stashko, C.W. Lin, J. Miner, C. Tyree, M. Nakane, P. Jacobson, and B.C. Lane J. Med. Chem. 44 2001 2879 2885
8. M.J. Coghlan, S.W. Elmore, P.R. Kym, and M.E. Cort Ann. Rep. Med. Chem. 37 2002 167 176
9. M.J. Coghlan, P.B. Jacobson, B. Lane, M. Nakane, C.W. Lin, S.W. Elmore, P.R. Kym, J.R. Luly, G.W. Carter, T. Russell, C.M. Tyree, J. Hu, M. Elgort, J. Rosen, and J.N. Miner Mol. Endocrinol. 17 2003 860 869
10. S.W. Elmore, M.J. Coghlan, D.D. Anderson, J.K. Pratt, B.E. Gren, A.X. Wang, M.A. Stashko, C.W. Lin, C.M. Tyree, J.N. Miner, P.B. Jacobson, D.M. Wilcox, and B.C. Lane J. Med. Chem. 44 2001 4481 4491
11. S.W. Elmore, J.K. Pratt, M.J. Coghlan, Y. Mao, B.E. Green, D.D. Anderson, M.A. Stashko, C.W. Lin, D. Falls, M. Nakane, L. Miller, C.M. Tyree, J.N. Miner, and B. Lane Bioorg. Med. Chem. Lett. 14 2004 1721 1727
12. P.R. Kym, M.E. Kort, M.J. Coghlan, J.L. Moore, R. Tang, J.D. Ratajczyk, D.P. Larson, S.W. Elmore, J.K. Pratt, M.A. Stashko, D.H. Falls, C.W. Lin, M. Nakane, L. Miller, C.M. Tyree, J.N. Miner, P.B. Jacobson, D.M. Wilcox, P. Nguyen, and B.C. Lane J. Med. Chem. 46 2003 1016 1030
13. H. Schäcke, A. Schottelius, W.-D. Döcke, P. Strehlke, S. Jaroch, S. Norbert, H. Rehwinkel, H. Hennekes, and K. Asadullah PNAS 101 2004 227 232
14. N. Shah, and T.S. Scanlan Bioorg. Med. Chem. Lett. 14 2004 5199 5203
15. R. Newton Thorax 55 2000 603 613
16. H. Schäcke, and H. Rehwinkel Curr. Opin. Investig. Drugs. 5 2004 524 528
17. R. Hirschmann, N.G. Steinberg, P. Buchschacher, J.H. Fried, G.J. Kent, M. Tishler, and S.L. Steelman J. Am. Chem. Soc. 85 1963 120 122
18. J.H. Fried, H. Mrozik, G.E. Arth, T.S. Bry, N.G. Steinberg, M. Tishler, R. Hirschmann, and S.L. Steelman J. Am. Chem. Soc. 85 1963 236 238
19. A. Ali, C.F. Thompson, J.M. Balkovec, D.W. Graham, M.L. Hammond, N. Quraishi, J.R. Tata, M. Einstein, L. Ge, G. Harris, T.M. Kelly, P. Mazur, S. Pandit, J. Santoro, A. Sitlani, C. Wang, J. Williamson, D.K. Miller, C.M. Thompson, D.M. Zaller, M.J. Forrest, E. Carballo-Jane, and S. Luell J. Med. Chem. 47 2004 2441 2452
20. J. Fried, A. Borman, W.B. Kessler, P. Grabowich, and E.F. Sabo J. Am. Chem. Soc. 80 1958 2338 2339
21. Z.G. Hajos, D.R. Parrish, S. Remington, D. Lust, and G. Saucy Org. Synth. 63 1985 26 36
22. Z.G. Hajos, D.R. Parrish, S. Remington, D. Lust, and G. Saucy Org. Synth. Coll. VII 1990 363 368
23. P. Buchschacher, A. Furst, P.S. Belica, P.S. Manchand, and G. Saucy Org. Synth. 63 1985 37 43
24. P. Buchschacher, A. Furst, J. Gutzwiller, P.S. Belica, P.S. Manchand, and G. Saucy Org. Synth. Coll. VII 1990 368 372
25. P. Ciceri, and F.W.J. Demnitz Tetrahedron Lett. 38 1997 389 390
26. A. Ray, and P.B. Sehgal J. Am. Soc. Nephrol. 2 1992 S214 S221
27. A. Ray, D.-H. Zhang, M.D. Siegel, and P. Ray Ann. N.Y. Acad. Sci. 762 1995 79 88
28. A. Waage, G. Slupphaug, and R. Shalaby Eur. J. Immunol. 20 1990 2439 2443
29. D.K. Granner, and G.M. Tomkins Methods Enzymol. 17A 1970 633 637
30. R. Minet, F. Villie, M. Marcollet, O. Meynial-Denis, and L. Cynober Clin. Chim. Acta 268 1997 121 132
31. W.B. Rowe, R.A. Ronzio, and V.P. Wellner Methods Enzymol. 17 1970 900 910
32. J.C. Santoro, G. Harris, and A. Sitlani Anal. Biochem. 289 2001 18 25
33. J.C. Gonzales, D.C. Johnson, D.C. Morrison, M.A. Freudenberg, C. Galanos, and R. Silverstein Infect. Immun. 61 1993 970 974
34. K.B. Sharpless, W. Amberg, Y.L. Bennani, G.A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.M. Wang, D. Xu, and X.-L. Zhang J. Org. Chem. 57 1992 2768 2771
35. A. Krief, W. Dumont, P. Pasau, and P. Lecomte Tetrahedron 45 1989 3039 3052
36. T. Onoda, R. Shirai, N. Kawai, and S. Iwasaki Tetrahedron 52 1996 13327 13338