4-Methyl-5-phenyl triazoles as selective inhibitors of 11β-hydroxysteroid dehydrogenase type I

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 11, 2008, Pages 3405-3411

  Zhu, Yuping ^a   Olson, Steven H ^a   Hermanowski Vosatka, Anne ^a   Mundt, Steven ^a   Shah, Kashmira ^a   Springer, Marty ^a   Thieringer, Rolf ^a   Wright, Samuel ^a   Xiao, Jianying ^a   Zokian, Hratch ^a   Balkovec, James M ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

11 HSD1; 4 Methyl 5 phenyl triazole; Metabolic syndrome

Indexed keywords

11BETA HYDROXYSTEROID DEHYDROGENASE; 11BETA HYDROXYSTEROID DEHYDROGENASE 1; 4 METHYL 5 PHENYL TRIAZOLE DERIVATIVE; ADAMANTYL TRIAZOLE; CORTISONE; HYDROCORTISONE; METHYL PHENYL CYCLOBUTYL TRIAZOLE; PHENYL CYCLOBUTYL TRIAZOLE; SULFONE DERIVATIVE; TRIAZOLE DERIVATIVE;

ARTICLE; CONTROLLED STUDY; DRUG INHIBITION; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; SINGLE DRUG DOSE; STRUCTURE ACTIVITY RELATION;

11-BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1; ANIMALS; COMBINATORIAL CHEMISTRY TECHNIQUES; DISEASE MODELS, ANIMAL; ENZYME INHIBITORS; HUMANS; MICE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 44149092411     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.04.013     Document Type: Article

References (26)

1. Maser E., and Oppermann U.C.T. Eur. J. Biochem. 249 (1997) 365
2. Agarwal A.K., Monder C., Eckstein B., and White P.C. J. Biol. Chem. 264 (1989) 18939
3. Albiston A.L., Obeyesekere V.R., Smith R.E., and Krozowski Z.S. Mol. Cell. Endocrinol. 105 (1994) R11
4. Funder J.W., Pearce P.T., Smith R., and Smith A.I. J. Clin. Endocrinol. Metab. 80 (1995) 2203
5. Peek P.M., Chrousos G.P., and Ann N.Y. Acad. Sci. 771 (1995) 665
6. Chapman K.E., Coutinho A., Gray M., Gilmour J.S., Savill J.S., and Secki J.R.. Ann. N.Y. Acad. Sci. 1088 (2006) 265
7. For a review see. White P.C., Mune T., and Agarwal A.K. Endocrinol. Rev. 18 (1997) 135
8. Kotelevtsev Y.V., Brown R.W., Fleming S., Edwards C.R., Seckl J.R., and Mullins J.J. J. Clin. Invest. 103 (1999) 683
9. Wilson R.C., Harbision M.D., Krozowski Z.S., Funder J.W., Shackleton C.H., Hanauske-Abel H.M., Wei J.Q., Hertecant J., Moran A., and Neiberger R.E. Clin. Endocrinol. Metab. 80 (1995) 3145
10. Monder C., Stewart P.M., Lakshmi V., Valentino R., Burt D., and Edwards C.R. Endocrinology 125 (1989) 1046
11. Gilmour J.S., Coutinho A.E., Cailhier J.-F., Man T.Y., Clay M., Thomas G., Harris H.J., Seckl J.R., Savill J.S., and Chapman K.E. J. Immunol. Res. 176 (2006) 7605
12. El Ayachi S., Paulmyer-Lacroix O., Verdier M., Alessi M.-C., Dutour A., and Grino M. Thromb. Haemost. 4 (2006) 621
13. Fotsch C., Askew B.C., and Chen J.J. Expert Opin. Ther. Patents 15 (2005) 289
14. Thieringer R., and Vosatka A.H. Expert Rev. Cardiovasc. Ther. 3 (2005) 911
15. Vosatka A.H., Balkovec J.M., Cheng K., Chen H.Y., Hernandez M., Koo G.C., Le Grand C.B., Li Z., Metzger J.M., Mundt S.S., Noonan H., Nunes C.N., Olson S.H., Pikounis B., Ren N., Robertson N., Schaeffer J.M., Shah K., Springer M.S., Strack A.M., Strowski M., Wu K., Wu T., Xiao J., Zhang B., Wright S.D., and Thieringer R. J. Exp. Med. 202 (2005) 517
16. Schweizer R.A.S., Atanasov A.G., Frey B.M., and Odermatt A. Mol. Cell. Endocrinol. 212 (2003) 41
17. Diederich S., Grossmann C., Hanke B., Quinkler M., Herrmann M., Bahr V., and Oelkers W. Eur. J. Endocrinol. 142 (2000) 200
18. Koch M.A., Wittenberg L.-O., Basu S., Jeyaraj D.A., Reinecke E., Gourzoulidou K., Odermatt A., and Waldmann H. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 16721
19. 3H]-cortisol are measured, and a percent inhibition is calculated. For a detailed description see. Koo G.C., Shah K., and Xiao J. PCT Int. Appl. (2004) 14 pp, WO 2004075831 A2 20040910
20. Olson S.H., Aster S.D., Brown K., Carbin L., Graham D.W., Hermanowski-Vosatka A., LeGrand C.B., Mundt S.S., Robbins M.A., Schaeffer J.M., Slossberg L.H., Szymonifka M.J., Thieringer R., Wright S.D., and Balkovec J.M. Bioorg. Med. Chem. Lett. 15 (2005) 4359 (sure and a percent inhibition is calculated)
21. Zhu, Y. et al. Bioorg. Med. Chem. Lett., in press.
22. Esser C.K., Bugianesi R.L., Caldwell C.G., Chapman K.T., Durette P.L., Girotra N.N., Kopka I.E., Lanza T.J., Levorse D.A., MacCoss M., Owens K.A., Ponpipom M.M., Simeone J.P., Harrison R.K., Niedzwiecki L., Becker J.W., Marcy A.I., Axel M.G., Christen A.J., McDonnell J., Moore V.L., Olszewski J.M., Saphos C., Visco D.M., Shen F., Colletti A., Krieter P.A., and Hagmann W.K. J. Med. Chem. 40 (1997) 1026
23. Ayumu K., Jean-François M., and Stephen L.B. Tetrahedron Lett. 40 (1999) 2657
24. Gao Y.-D., Olson S.H., Balkovec J.M., Zhu Y., Royo I., Ismail J., Hartley D., and Mosley R. Xenobiotica 37 (2007) 124
25. Li W., Nelson D.P., Jensen M.S., Hoerrner R.S., Cai D., Larsen R.D., and Reider P.J. J. Org. Chem. 67 (2002) 5394
26. Collman J.P., Zhong M., Zhang C., and Costanzo S. J. Org. Chem. 66 (2001) 7892