Ring nitrogen-substituted non-steroidal estrogens: Pyridine and pyrimidine analogs of the phenol in deoxyhexestrol experience resonance constraints on preferred ligand conformation

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 23, 2004, Pages 5835-5839

  De Angelis, Meri ^a   Katzenellenbogen, John A ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Estrogen; Ligand; Pyridine; Pyrimidine

Indexed keywords

ESTROGEN; ESTROGEN RECEPTOR BETA; LIGAND; PHENOL; PYRIDINE; PYRIDINOL; PYRIMIDINE DERIVATIVE;

ARTICLE; BINDING AFFINITY; CONFORMATION; RECEPTOR BINDING; SUBSTITUTION REACTION;

ESTROGENS, NON-STEROIDAL; HUMANS; LIGANDS; MOLECULAR CONFORMATION; PHENOLS; PROTEIN BINDING; PYRIDINES; PYRIMIDINES;

EID: 7244220264     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.09.048     Document Type: Article

References (24)

1. N.E. Davidson N. Engl. J. Med. 352 1995 1638
2. E. Barrett-Conner, and T.L. Bush J. Am. Med. Assoc. 265 1991 1861
3. K. Yaffe, G. Sawaya, I. Lieberbung, and D. Grady J. Am. Med. Assoc. 279 1998 688
4. S.A. Beresford, N.S. Weiss, L.F. Voigt, and B. McKnight Lancet 349 1997 458
5. M. Dutertre, and C.L. Smith J. Pharm. Exp. Ther. 295 2000 431
6. S. Mosselman, J. Polman, and R. Dijekema FEBS Lett. 392 1996 49
7. G.G.J.M. Kuiper, E. Enmark, M. Pelto-Huikko, S. Nilsson, and J.-Å. Gustafsson PNAS 93 1996 5925
8. A.C.W. Pinke, A.M. Brzozowski, R.E. Hubbard, T. Bonn, A.-G. Thorsell, O. Engström, J. Ljunggren, J.-Å. Gustafsson, and M. Carlquist EMBO J. 18 1999 4608
9. J. Sun, M.J. Meyers, B.E. Fink, R. Rajendran, J.A. Katzenellenbogen, and B.S. Katzenellenbogen Endocrinology 140 1999 800
10. D.S. Mortensen, A.L. Rodriguez, K.E. Carlson, J. Sun, B.S. Katzenellenbogen, and J.A. Katzenellenbogen J. Med. Chem. 44 2001 3838
11. G.G.J.M. Kuiper, B. Carlsson, J. Grandien, E. Enmark, J. Häggblad, S. Nilsson, and J.-Å. Gustafsson Endocrinology 138 1997 863
12. U. Schopfer, P. Schoeffter, S.F. Bischoff, J. Nozulak, D. Feuerbach, and P. Floersheim J. Med. Chem. 45 2002 1399
13. M.J. Meyers, J. Sun, K.E. Carlson, G.A. Marriner, B.S. Katzenellenbogen, and J.A. Katzenellenbogen J. Med. Chem. 44 2001 4230
14. AstraZeneca A. B. WO Patent 02/051821-A1, 2002
15. AstraZeneca A. B. WO Patent 02/46168-A1, 2002
16. Wyeth, WO Patent 03/050095-A1, 2003
17. R.J. Edsall, H.A. Harris, E.R. Manas, and R.E. Mewshaw Bioorg. Med. Chem. 11 2003 3457
18. B.R. Henke, D.H. Drewry, S.A. Jones, E.L. Stewart, S.L. Weaver, and R.W. Wiethe Bioorg. Med. Chem. Lett. 11 2001 1939
19. B.R. Henke, T.G. Consler, N. Go, R.L. Hale, D.R. Hohman, S.A. Jones, A.T. Lu, L.B. Moore, J.T. Moore, L.A. Orband-Miller, R.G. Robinett, J. Shearin, P.K. Spearing, E.L. Stewart, P.S. Turnbull, S.L. Weaver, S.P. Williams, G.B. Wisley, and M.H. Lambert J. Med. Chem. 45 2002 5492
20. A. Bouillon, J.-C. Lancelot, V. Collot, P.R. Bovy, and S. Rault Tetrahedron 58 2002 2885
21. G.R. Krow, Y. Xiao, K. Cannon, S.A. Swan, and A. Nickel Synth. Commun. 30 22 2000 4093
22. K.E. Carlson, I. Choi, A. Gee, B.S. Katzenellenbogen, and J.A. Katzenellenbogen Biochemistry 1997 14897
23. M.R. Kilbourn, A.J. Arduengo, J.T. Park, and J.A. Katzenellenbogen Mol. Pharmacol. 19 1981 388
24. A.K. Shiau, D. Barstad, P.M. Loria, L. Cheng, P.J. Kushner, D.A. Agard, and G.L. Greene Cell 95 1998 927