Synthesis and evaluation of 17α-E-20-(heteroaryl)norpregn-1,3,5(10), 20 tetraene-3,17β-diols [17α-(heteroaryl)vinyl estradiols] as ligands for the estrogen receptor-α ligand binding domain (ERα-LBD)

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 2, 2012, Pages 977-979

  Olmsted, Sandra L ^a   Tongcharoensirikul, Pakamas ^b   McCaskill, Emmett ^b   Gandiaga, Karla ^b   Labaree, David ^c   Hochberg, Richard B ^c   Hanson, Robert N ^b  

^a AUGSBURG COLLEGE   (United States)

^b NORTHEASTERN UNIVERSITY   (United States)

^c YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Alkaline phosphatase induction; Competitive binding assay; Estrogen receptor ligand binding domain; Heteroarylvinyl estradiols; Relative binding affinity; Relative stimulatory activity

Indexed keywords

17ALPHA E 20 (HETEROARYL)NORPREGN 1,3,5(10),20 TETRAENE 3,17BETA DIOLS [17AALPHA (HETEROARYL)VINYL ESTRADIOLS]; ESTRADIOL DERIVATIVE; ESTROGEN RECEPTOR ALPHA; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL INTERACTION; DRUG SCREENING; DRUG SYNTHESIS; LIGAND BINDING; PROTEIN DOMAIN;

BINDING SITES; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; LIGANDS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84855671710     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.12.003     Document Type: Article

References (29)

1. M.J. Tsai, and B.W. O'Malley Annu. Rev. Biochem. 63 1994 451
2. S. Nilsson, and J.-A. Gustafsson Crit. Rev. Biochem. Mol. Biol. 37 2002 1
3. R.M. Evans Science 240 1988 889
4. B.S. Katzenellenbogen, I. Choi, R. Delage-Mourroux, T.R. Ediger, P.G.V. Martini, M. Montano, J. Sun, K. Weis, and J.A. Katzenellenbogen J. Steroid Biochem. Mol. Biol. 74 2000 279
5. M. Duterte, and C.L. Smith J. Pharmacol. Exp. Ther. 295 2000 431
6. L.L. Hart, and J.R. Davie Biochem. Cell Biol. 80 2002 335
7. N.J. McKenna, and B.W. O'Malley J. Steroid Biochem. Mol. Biol. 74 2000 351
8. V. Krishnan, H. Heath, and H.U. Bryant Vitam. Horm. 60 2001 123
9. J.I. Macgregor, and V.C. Jordan Pharmacol. Rev. 50 1998 151
10. V.C. Jordan J. Med. Chem. 46 2003 883
11. V.C. Jordan J. Med. Chem. 46 2003 1081
12. A.M. Brzozowski, A.C. Pike, Z. Dauter, R.E. Hubbard, T. Bonn, O. Engstrom, L. Ohman, G.L. Greene, J.A. Gustafsson, and M. Carlquist Nature 389 1997 753
13. A.K. Shiau, D. Barstad, P.M. Loria, L. Cheng, P.J. Kushner, D.A. Agard, and G.L. Greene Cell 95 1998 927
14. D.M. Tanenbaum, Y. Wang, S.P. Williams, and P.B. Sigler Proc. Natl. Acad. Sci. U.S.A. 95 1998 5998
15. A.C.W. Pike, A.M. Brzozowski, R.E. Hubbard, T. Bonn, A.-G. Thorsell, O. Engstrom, J. Ljunggren, J.-A. Gustafsson, and M. Carlquist EMBO J. 18 1999 4608
16. E. Napolitano, R. Fiaschi, and R.N. Hanson J. Med. Chem. 34 1991 2754
17. E. Napolitano, R. Fiaschi, L.W. Herman, and R.N. Hanson Steroids 61 1996 384
18. R.N. Hanson, L.W. Herman, R. Fiaschi, and E. Napolitano Steroids 61 1996 718
19. R.N. Hanson, C.Y. Lee, C.J. Friel, R. Dilis, A. Hughes, and E.R. DeSombre J. Med. Chem. 46 2003 2865
20. R.N. Hanson, C.J. Friel, R. Dilis, A. Hughes, and E.R. DeSombre J. Med. Chem. 48 2005 4300
21. J.A. Mobley, J.O. L'Esperance, M. Wu, C.J. Friel, R.N. Hanson, and S.-M. Ho Mol. Cancer. Ther. 3 2004 587
22. R.N. Hanson, C.Y. Lee, C. Friel, A. Hughes, and E.R. DeSombre Steroids 68 2003 143
23. R.N. Hanson, R. Dilis, P. Tongcharoensirikul, A. Hughes, and E.R. DeSombre J. Med. Chem. 50 2007 472
24. K.W. Nettles, J.B. Bruning, G. Gil, E.E. O'Neill, J. Nowak, A. Hughes, Y. Kim, E.R. DeSombre, R. Dilis, and R.N. Hanson EMBO Rep. 8 2007 563
25. D.C. Labaree, J. Shang, H.A. Harris, C. O'Connor, T.Y. Reynolds, and R.B. Hochberg J. Med. Chem. 46 2003 1886
26. S. Green, P. Walter, V. Kumar, A. Krust, J.M. Bonert, P. Argos, and P. Chambon Nature 320 1986 134
27. B.A. Littlefield, E. Gurpide, L. Markiewicz, B. McKinley, and R.B. Hochberg Endocrinology 127 1990 2757
28. C.W. Bird, and G.W.H. Cheeseman A.R. Katritzky, C.W. Rees, Comprehensive Heterocyclic Chemistry Vol. 4 1984 Pergamon Press New York, NY 1 39
29. C.D. Johnson A.R. Katritzky, C.W. Rees, Comprehensive Heterocyclic Chemistry Vol. 2 1984 Pergamon Press New York, NY 99 164