Synthesis of 17-alpha-substituted arylvinyl estradiols and evaluation as ligands for the estrogen receptor ligand binding domain (ER-LBD)

MEDI 332

Robert N. Hanson, r.hanson@neu.edu1, Sandra Olmsted, olmsteds@augsburg.edu2, Pakamas Tongcharoensirikul, p.tongcharoensirikul@neu.edu1, Emmett McCaskill, r.hanson@neu.edu1, David C. Labaree3, and Richard B. Hochberg3. (1) Department of Chemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, MA 02115, (2) Deaprtment of Chemistry, Augsburg College, 2211 Riverside Avenue South, Minneapolis, MN 55454, (3) Department of Obstetrics and Gynecology, Yale University School of Medicine, New Haven, CT 06510
As part of our program to probe the ligand binding pocket of the estrogen receptor we have prepared and evaluated new examples of 17-alpha-(substituted phenyl) vinyl estradiols. Previous results from competitive binding assays indicated that the affinity for the ER-LBD is dependent upon the nature and site of substitution but that translation to efficacy in Ishikawa cells was often inconsistent. In this study we describe the preparation of different (substituted phenyl) vinyl analogs and their evaluation as ligands for the ER-LBD in order to explore the relationship between binding and stimulation.

Supported by grants from NIH [PHS 1RO1 CA81409] and the U.S. Army Breast Cancer Research Program [DAMD 17-99-1-9333 and 17-00-1-00384].

 

Poster Session
7:00 PM-9:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 20, 2007 BCEC -- Exhibit Hall - B2, Sci-Mix

Division of Medicinal Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007