Thyroid receptor ligands. Part 2: Thyromimetics with improved selectivity for the thyroid hormone receptor beta

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 13, 2004, Pages 3549-3553

  Hangeland, Jon J ^a   Doweyko, Arthur M ^a   Dejneka, Tamara ^a   Friends, Todd J ^a   Devasthale, Pratik ^a   Mellström, Karin ^b   Sandberg, Johnny ^b   Grynfarb, Marlena ^b   Sack, John S ^a   Einspahr, Howard ^a,c   Färnegårdh, Mathias ^b   Husman, Bolette ^b   Ljunggren, Jan ^b   Koehler, Konrad ^b   Sheppard, Cheryl ^a,d   Malm, Johan ^b   Ryono, Denis E ^a  

^a BRISTOL MYERS SQUIBB   (United States)

^b Karo Bio   (Sweden)

^c Cardinal Health PTS Inc ^*  (United States)

^d Cardinal Health   (United States)

Author keywords

Thyroid hormone receptor; Thyromimetics

Indexed keywords

LIGAND; METHIONINE; PHENYL GROUP; THYROID HORMONE RECEPTOR BETA; THYROID HORMONE RECEPTOR BETA1; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; DRUG ACTIVITY; DRUG POTENCY; DRUG RECEPTOR BINDING; HYDROPHOBICITY; RECEPTOR INTRINSIC ACTIVITY; STRUCTURE ACTIVITY RELATION; X RAY DIFFRACTION;

2-PROPANOL; AMINO ACIDS; BINDING SITES; CELL LINE; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; INHIBITORY CONCENTRATION 50; LIGANDS; STRUCTURE-ACTIVITY RELATIONSHIP; THYROID HORMONE RECEPTORS BETA; THYROID HORMONES; TRIIODOTHYRONINE;

EID: 2942596255     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.04.032     Document Type: Article

References (25)

1. Brent G. Endocrinology: Basic and Clinical Principles. 1997;Humana, Totowa, NJ. Chapter 19
2. Lazar M.A. Endocr. Rev. 14:1993;184
3. Forrest D. Semin. Cancer Biol. 5:1994;167
4. Wilkström L., Johansson C., Saltó C., Barlow C., Barrow A.G., Baas F., Forrest D., Thorén P., Vennström B. EMBO J. 17:1998;455
5. Johansson C., Göthe S., Forrest D., Vennström B., Thorén P. Am. J. Physiol. 276:1999;H2006
6. Trost S.U., Swanson E., Gloss B., Wang-Iverson D.B., Zhang H., Volodarsky T., Grover G.J., Baxter J.D., Chiellini G., Scanlan T.S., Dillmann W.H. Endocrinology. 141:2000;3057
7. Grover G.J., Mellström K., Ye L., Malm J., Li Y.-L., Bladh L.-G., Sleph P.G., Smith M.A., George R., Vennström B., Mookhtiar K., Horvath R., Speelman J., Egan D., Baxter J.D. PNAS. 100:2003;10067
8. Ye L., Li Y.-L., Mellström K., Bladh L.-G., Koehler K., Garg N., Garcia Collazo A.M., Litten C., Husman B., Persson K., Ljunggren J., Grover G., Sleph P.G., George R., Malm J. J. Med. Chem. 46:2003;1580
9. Underwood A.H., Emmett J.C., Ellis D., Flynn S.B., Leeson P.D., Benson G.M., Movelli R., Pearce N.J., Shah V.P. Nature. 324:1986;425
10. Dow R.L., Schneider S.R., Paight E.S., Hank R.F., Chaing P., Cornelius P., Lee E., Newsome W.P., Swick A., Spitzer J., Hargrove D.E., Patterson T.A., Pandit J., Chrunyk B.A., LeMotte P.K., Danley D.E., Rosner M.H., Ammirati M.J., Simones S.P., Schulte G.K., Tate B.F., DaSilva-Jardine P. Bioorg. Med. Chem. Lett. 13:2003;379
11. Borngraeber S., Budny M.-J., Chiellini G., Cunha-Lima S.T., Togashi M., Webb P., Baxter J.D., Scanlan T.S., Fletterick R.J. PNAS. 100:2003;15358
12. 5, 11
13. Woltz J.H., Buco S.N. J. Org. Chem. 20:1955;210
14. Yokoyama N., Walker G.N., Main A.J., Stanton J.L., Morrissey M.M., Boehm C., Engle A., Meubert A.D., Wasvary J.M., Stephan Z.F., Steele R.E. J. Med. Chem. 38:1995;695
15. Ishiyama T., Murata M., Miyaura N.J. Org. Chem. 60:1995;7508
16. Carlsson B., Singh B.N., Temciuc M., Nilsson S., Li Y.-L., Mellin C., Malm J. J. Med. Chem. 45:2002;623
17. Barkhem T., Carlsson B., Simons J., Moeller B., Berkenstam A., Gustafsson J.-Å., Nilsson S. J. Steroid Biochem. Mol. Biol. 38:1991;667
18. 16 The final structure has an Rfree of 34.7 and Rwork of 26.1. The final geometry is good (rmsd for distance is 0.015 Å and for angle is 1.5°). The coordinates have been deposited at www.rcsb.org (1r6g.pdb)
19. Otwinowski Z., Minor W. Carter C.W., Sweets R.M. Methods in Enzymology. Vol. 276:1997;307-326 Academic, New York
20. Navaza J. Acta Cryst. A50:1994;157
21. Winn M.D., Isupov M.N., Murshudov G.N. Acta Cryst. D57:2001;122
22. Jones T.A., Zou J.Y., Cowan S.W., Kjeldgaard M. Acta Cryst. A47(part 2):1991;110
23. McMartin C., Bohacek R.S. J. Comput.-Aided Mol. Des. 11:1997;333. Flo(qxp) is a molecular mechanics modeling program available from Colin McMartin, Thistlesoft, PO Box 227, Colebrook, CT 06021, USA
24. Webb P., Nguyen N.-H., Chiellini G., Yoshihara H.A.I., Cunha Lima S.T., Apriletti J.W., Riberio R.C.J., Marimuthu A., West B.L., Goede P., Mellström K., Nillson S., Kushner P.J., Fletterick R.J., Scanlan T.S., Baxter J.D. J. Steroid Biochem. Mol. Biol. 83:2003;59-73
25. Nguyen N.-H., Apriletti J.W., Cunha Lima S.T., Webb P., Baxter J.D., Scanlan T.S. J. Med. Chem. 45:2002;3310