Sulfonylthiadiazoles with an Unusual Binding Mode as Partial Dual Peroxisome Proliferator-Activated Receptor (PPAR) γ/δ Agonists with High Potency and invivo Efficacy

ChemMedChem

Volumn 6, Issue 4, 2011, Pages 633-653

  Keil, Stefanie ^a   Matter, Hans ^a   Schönafinger, Karl ^a   Glien, Maike ^a   Mathieu, Magali ^a   Marquette, Jean Pierre ^a   Michot, Nadine ^a   Haag Diergarten, Silke ^a   Urmann, Matthias ^a   Wendler, Wolfgang ^a  

^a SANOFI AVENTIS DEUTSCHLAND GMBH   (Germany)

Author keywords

Agonists; Diabetes; Drug discovery; Peroxisome proliferator activated receptors; X ray crystallography

Indexed keywords

[2 METHYL 4 [4 METHYL 2 (4 TRIFLUOROMETHYLPHENYL) 5 THIAZOLYLMETHYLTHIO]PHENOXY]ACETIC ACID; BENZAMIDE; PARTIAL AGONIST; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR AGONIST; ROSIGLITAZONE; SULFONYLTHIADIAZOLE; THIADIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DRUG BINDING; DRUG CONFORMATION; DRUG EFFICACY; DRUG HALF LIFE; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; GLUCOSE METABOLISM; HYDROGEN BOND; IN VIVO STUDY; METABOLIC SYNDROME X; NONHUMAN; PRIORITY JOURNAL; PROTEIN LIPID INTERACTION; WEIGHT GAIN;

ANIMALS; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; DIABETES MELLITUS, EXPERIMENTAL; DIABETES MELLITUS, TYPE 2; MICE; PPAR DELTA; PPAR GAMMA; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONES; THIADIAZOLES;

EID: 79953034919     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201100047     Document Type: Article

References (62)

1. H. King, M. Rewers, Diabetes Care 1993, 16, 157-177;
2. P. G. Kopelman, G. A. Hitman, Lancet 1998, 352 (Suppl.4), SIV5.
3. R. H. Eckel, S. M. Grundy, P. Z. Zimmet, Lancet 2005, 365, 1415-1428.
4. K. Motojima, Cell Struct. Funct. 1993, 18, 267-277.
5. S. Luquet, C. Gaudel, D. Holst, J. Lopez-Soriano, C. Jehl-Pietri, A. Fredenrich, P. A. Grimaldi, Biochim. Biophys. Acta 2005, 1740, 313-317.
6. B. Staels, J.-C. Fruchart, Diabetes 2005, 54, 2460-2470.
7. J. P. Berger, T. E. Akiyama, P. T. Meinke, Trends Pharmacol. Sci. 2005, 26, 244-251.
8. P. T. W. Cheng, R. Mukherjee, Mini-Rev. Med. Chem. 2005, 5, 741-753.
9. P. D. Pelton, M. Patel, K. T. Demarest, Curr. Top. Med. Chem. 2005, 5, 265-282.
10. A. Berkenstam, J.-A. Gustafsson, Curr. Opin. Pharmacol. 2005, 5, 171-176.
11. G. J. Etgen, N. Mantlo, Curr. Top. Med. Chem. 2003, 3, 1649- 1661.
12. T. M. Willson, P. J. Brown, D. D. Sternbach, B. R. Henke, J. Med. Chem. 2000, 43, 527-550.
13. H. Keller, C. Dreyer, J. Medin, A. Mahfoudi, K. Ozato, W. Wahli, Proc. Natl. Acad. Sci. USA 1993, 90, 2160-2164.
14. T. Gulick, S. Cresci, T. Caira, D. D. Moore, D. P. Kelly, Proc. Natl. Acad. Sci. USA 1994, 91, 11012-11016.
15. B. M. Forman, J. Chen, R. M. Evans, Proc. Natl. Acad. Sci. USA 1997, 94, 4312-4317.
16. P. Tontonoz, E. Hu, B. M. Spiegelman, Cell 1994, 79, 1147-1156.
17. S. M. Rangwala, M. A. Lazar, Trends Pharmacol. Sci. 2004, 25, 331-336.
18. C. Day, Diabetic Med. 1999, 16, 179-192.
19. X.-Y. Wang, C. H. Lee, S. Tiep, R. T. Yu, J. Ham, H. Kang, R. M. Evans, Cell 2003, 113, 159-170.
20. Y.-X. Wang, C.-L. Zhang, R. T. Yu, H. K. Cho, M. C. Nelson, C. R. Bayuga-Ocampo, J. Ham, H. Kang, R. M. Evans, PLoS Biol. 2004, 2, 1532-1539.
21. M. D. Leibowitz, C. Fievet, N. Hennuyer, J. Peinado-Onsurbe, H. Duez, J. Berger, C. A. Cullinan, C. P. Sparrow, J. Baffic, G. D. Berger, C. Santini, R. W. Marquis, R. L. Tolman, R. G. Smith, D. E. Moller, J. Auwerx, FEBS Lett. 2000, 473, 333-336.
22. T. Tanaka, J. Yamamoto, S. Iwasaki, H. Asaba, H. Hamura, Y. Ikeda, M. Watanabe, K. Magoori, R. Ioka, K. Tachibana, Y. Watanabe, Y. Uchiyama, K. Sumi, H. Iguchi, S. Ito, T. Doi, T. Hamakubo, M. Naito, J. Auwerx, M. Yanagisawa, T. Kodama, J. Sakai, Proc. Natl. Acad. Sci. USA 2003, 100, 15924-15929.
23. V. A. Narkar, M. Downes, R. T. Yu, E. Embler, Y.-X. Wang, E. Banayo, M. M. Mihaylova, M. C. Nelson, Y. Zou, H. Juguilon, H. Kang, R. J. Shaw, R. M. Evans, Cell 2008, 134, 405-415.
24. W. R. Oliver, Jr., J. L. Shenk, M. R. Snaith, C. S. Russell, K. D. Plunket, N. L. Bodkin, M. C. Lewis, D. A. Winegar, M. L. Sznaidman, M. H. Lambert, H. E. Xu, D. D. Sternbach, S. A. Kliewer, B. C. Hansen, T. M. Willson, Proc. Natl. Acad. Sci. USA 2001, 98, 5306-5311.
25. L. N. Khlaponina, V. V. Moroz, V. D. Brutov, A. G. Selichenko, Khimiko-Farmatsevticheskii Zhurnal 1987, 21, 965-968.
26. PDB files taken from RCSB Protein Database: ;
27. F. C. Bernstein, T. F. Koetzle, G. J. B. Williams, E. F. Meyer, M. D. Brice, J. R. Rodgers, O. Kennard, T. Shimanouchi, M. Tasumi, J. Mol. Biol. 1977, 112, 535-542;
28. J. W. Berman, F. Zukang, G. Gilliland, T. N. Bhat, H. Weissig, I. N. Shindyalov, P. E. Bourne, Nucl. Acids Res. 2000, 28, 235-242.
29. H. E. Xu, M. H. Lambert, V. G. Montana, D. J. Parks, S. G. Blanchard, P. J. Brown, D. D. Sternbach, J. M. Lehmann, G. B. Wisely, T. M. Wilson, S. A. Kliever, M. V. Milburn, Mol. Cell 1999, 3, 397-403.
30. W. Heiden, T. Goetze, J. Brickmann, J. Comput. Chem. 1993, 14, 246-250;
31. J. Brickmann, H. Bertling, B.M. Bussian, T. Goetze, M. Knoblauch, M. Waldherr-Teschner, Tagungsber.-Vortragstag., Ges. Dtsch. Chem. Fachgruppe Chem.-Inf. 1987, 93-111.
32. W. Heiden, G. Moeckel, J. Brickmann, J. Comput.-Aided Mol. Des. 1993, 7, 503-514.
33. A. Ghose, G. Crippen, J. Comput. Chem. 1986, 7, 565-577;
34. V. N. Viswanadhan, A. K. Ghose, G. R. Revankar, R. K. Robins, J. Chem. Inf. Model. 1989, 29, 163-172.
35. M. L. Connolly, Science 1983, 221, 709-713;
36. M. L. Connolly, J. Appl. Crystallogr. 1983, 16, 548-558.
37. W. Bourguet, M. Ruff, P. Chambon, H. Gronemeyer, D. Moras, Nature 1995, 375, 377-382.
38. C. McMartin, R. S. Bohacek, J. Comput.-Aided Mol. Des. 1997, 11, 333-344.
39. B. Kuhn, P. Mohr, M. Stahl, J. Med. Chem. 2010, 53, 2601-2611.
40. R. D. Cramer, D. E. Patterson, J. E. Bunce, J. Am. Chem. Soc. 1988, 110, 5959-5967.
41. M. Clark, R. D. Cramer, D. M. Jones, D. E. Patterson, P. E. Simeroth, Tetrahed. Comp. Meth. 1990, 3, 47-59.
42. 3D-QSAR in Drug Design: Theory, Methods and Applications, (Ed.: H. Kubinyi), Kluwer/Escom, Dordrecht (The Netherlands), 1993.
43. Z.-L. Wei, A. P. Kozikowski, J. Org. Chem. 2003, 68, 9116-9118.
44. P. J. Brown, T. A. Smith-Oliver, P. S. Charifson, N. C. O. Tomkinson, A. M. Fivush, D. D. Sternbach, L. E. Wade, L. Orband-Miller, D. J. Parks, S. G. Blanchard, Chem. Biol. 1997, 4, 909-918.
45. Collaborative Computational Project, Number4, Acta Crystallogr. Sect. D: Biol. Crystallogr. 1994, 50, 760-763.
46. J. Navaza, Acta Crystallogr. Sect. A: Found. Crystallogr. 1994, 50, 157-163.
47. P. Roversi, E. Blanc, C. Vonrhein, G. Evans, G. Bricogne, Acta Crystallogr. Sect. D: Biol. Crystallogr. 2000, 56, 1316-1323.
48. A. T. Brünger, P. D. Adams, G. M. Clore, W. L. DeLano, P. Grose, R. W. Grosse-Kunstleve, J.-S. Jiang, J. Kuszewskic, M. Nilges, N. S. Pannuh, R. J. Read, L. M. Rice, T. Simonson, G. L. Warren, Acta Crystallogr. Sect. D: Biol. Crystallogr. 1998, 54, 905-921.
49. P. J. Goodford, J. Med. Chem. 1985, 28, 849-857.
50. S. J. Weiner, P. A. Kollman, D. A. Case, U. C. Singh, C. Ghio, G. Algona, S. Profeta, P. Weiner, J. Am. Chem. Soc. 1984, 106, 765-784.
51. SYBYL Molecular Modeling Package (version8.0), Tripos Ltd, St.Louis, MO (USA), 2009.
52. T. Halgren, J. Am. Chem. Soc. 1990, 112, 4710-4723;
53. T. Halgren, J. Comput. Chem. 1999, 20, 720-729.
54. S. Wold, Technometrics 1978, 20, 397-405;
55. P. Diaconis, B. Efron, Sci. Am. 1983, 248, 116-130;
56. R. D. Cramer, J. D. Bunce, D. E. Patterson, Quant. Struct.-Act. Relat. 1988, 7, 18-25.
57. R. P. Sheridan, R. B. Nachbar, B. L. Bush, J. Comput.-Aided Mol. Des. 1994, 8, 323-340.
58. S. Wold, C. Albano, W. J. Dunn, U. Edlund, K. Esbenson, P. Geladi, S. Hellberg, W. Lindberg, M. Sjöström in Chemometrics: Mathematics and Statistics in Chemistry, (Ed.: B.R. Kowalski), Kluwer Academic Publishers, Dortrecht (The Netherlands), 1984, pp.17-95;
59. W. J. Dunn, S. Wold, U. Edlund, S. Hellberg, J. Gasteiger, Quant. Struct.-Act. Relat. 1984, 3, 131;
60. P. Geladi, J. Chemom. 1988, 2, 231-246.
61. M. Clark, R. D. Cramer, Quant. Struct.-Act. Relat. 1993, 12, 137-145.
62. S. Keil, H. Matter, K. Schönafinger, M. Urmann, M. Glien, W. Wendler, H.-L. Schäfer, E. Falk, (Sanofi-Aventis GmbH, Frankfurt am Main, Germany), PCT Int. Appl. WO2007/039175, 2007.