Discovery of a potent series of non-steroidal non α-trifluoromethyl carbinol glucocorticoid receptor agonists with reduced lipophilicity

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 4, 2011, Pages 1126-1133

  Diallo, Hawa ^a   Angell, Davina C ^a   Barnett, Heather A ^a   Biggadike, Keith ^a   Coe, Diane M ^a   Cooper, Tony W J ^a   Craven, Andy ^a   Gray, James R ^a   House, David ^a   Jack, Torquil I ^a   Keeling, Steve P ^a   MacDonald, Simon J F ^a   McLay, Iain M ^a   Oliver, Samuel ^a   Taylor, Simon J ^a   Uings, Iain J ^a   Wellaway, Natalie ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Glucocorticoid; Indazole; Low lipophilicity; Meta channel; Non steroidal; Sulfonamide

Indexed keywords

ALPHA TRIFLUOROMETHYLCARBINOL; GLUCOCORTICOID; GLUCOCORTICOID RECEPTOR AGONIST; HORMONE RECEPTOR AFFECTING AGENT; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDAZOLE DERIVATIVE; SULFONAMIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; DRUG BINDING; DRUG EFFECT; DRUG POTENCY; DRUG STRUCTURE; LIPOPHILICITY; MOLECULAR INTERACTION; NONHUMAN; RAT;

BINDING SITES; CELL LINE, TUMOR; COMPUTER SIMULATION; DRUG EVALUATION, PRECLINICAL; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; INDAZOLES; RECEPTORS, GLUCOCORTICOID; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 79851511831     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.12.121     Document Type: Article

References (20)

1. B.P. Schimmer, and K.L. Parker J.G. Hardman, L.E. Limbird, A.G. Gilman, Goodmans the Pharmacological Basis of Therapeutics 2001 McGraw-hill New York 1649
2. H. Schäcke, W.D. Docke, and K. Asdullah Parmacol. Ther. 96 2002 23
3. M. Resche-Rigon, and H. Gronemeyer Curr. Opin. Chem. Biol. 2 1998 501
4. P.J. Barnes Clin. Sci. 94 1998 557
5. L. Buckbinder, and R.P. Robinson Curr. Drug Targets Inflamm. Allergy 1 2002 127
6. H. Schäcke, M. Berger, T.G. Hansson, D. McKerrecher, and H. Rehwinkel Expert Opin. Ther. Patents 18 2008 339
7. M.L. Mohler, Y. He, Z. Wu, S. Hong, and D.D. Miller Expert Opin. Ther. Patents 17 2007 37
8. A.S. Veleiro, L.D. Alvarez, S.L. Eduardo, and G. Burton ChemMedChem 5 2010 649
9. J. Regan, H. Razavi, and D. Thomson J. Annu. Rep. Med. Chem. 43 2008 141
10. T. Chen Curr. Opin. Chem. Biol. 12 2008 418
11. H. Schäcke, K. Asadullah, M. Berger, and H. Rehwinkel E. Ottow, H. Weinmann, Nuclear Receptors as Drug Targets 2008 Wiley-VCH Weinheim 305
12. M. Clackers, D.M. Coe, D.A. Demaine, G.W. Hardy, D. Humphreys, G.G.A. Inglis, M.J. Johnston, H.T. Jones, D. House, R. Loiseau, D.J. Minck, P.A. Skone, I. Uings, I.M. McLay, and S.J.F. Macdonald Bioorg. Med. Chem. Lett. 17 2007 4737
13. H.A. Barnett, D.M. Coe, A.W.J. Cooper, T.I. Jack, H.T. Jones, S.J.F. Macdonald, I.M. McLay, N. Rayner, R.Z. Sasse, T.J. Shipley, P.A. Skone, G.I. Somers, S. Taylor, I.J. Uings, J.M. Woolven, and G.G. Weingarten Bioorg. Med. Chem. Lett. 19 2009 158
14. K. Biggadike, M. Caivano, M. Clackers, D.M. Coe, G.W. Hardy, D. Humphreys, H.T. Hones, D. House, A. Miles-Williams, P.A. Skone, I. Uings, V. Weller, I.M. McLay, and S.J.F. Macdonald Bioorg. Med. Chem. Lett. 19 2009 4846
15. K.P. Madauss, R.K. Bledsoe, I. McLay, E.L. Stewart, I.J. Uings, G. Weingarten, and S.P. Williams Bioorg. Med. Chem. Lett. 18 2008 6097
16. K. Biggadike, R.K. Bledsoe, D.M. Coe, T.W.J. Cooper, D. House, M.A. Iannone, S.J.F. Macdonald, K.P. Madauss, I.M. McLay, T.J. Shipley, S.J. Taylor, T.B. Tran, I.J. Uings, V. Weller, and S.P. Williams Prog. Natl. Acad. Sci. U.S.A. 106 2009 18114
17. R. Betageri, Y. Zhang, R.M. Zindell, D. Kuzmich, T.M. Kirrane, J. Bentzien, L. Zuvela-Jelaska, G. Nabozny, and D.S. Thomson Bioorg. Med. Chem. Lett. 15 2005 4761
18. D.R. Marshall, G. Rodriquez, D.S. Thomson, and C.A. Nelson Bioorg. Med. Chem. Lett. 17 2007 315
19. J.C. Antilla, A. Klapars, X. Huang, and S.L. Buchwald J. Am. Chem. Soc. 123 2001 7727
20. c log P calculated with Daylight software.