Structure-activity relationships of four 11-hydroxyestrones isomeric at the C-9 and C-11 positions.
The synthesis of 11 alpha-hydroxyestrone, 11 alpha-hydroxy-9 beta-estrone, and 11 beta-hydroxy-9 beta-estrone are presented. The reduction of 11-keto-9 beta-estrone 17-ethyleneketal by sodium in ethanol or sodium borohydride resulted in 11-hydroxy-9 beta-estrones. The 11-hydroxyl group configurations were opposite to expectations: sodium in boiling ethanol afforded the axial 11 beta-hydroxy-9 beta-estrone, while sodium borohydride in boiling tetrahydrofuran gave the equatorial 11 alpha-hydroxy-9 beta-estrone. In immature rat uterotropic bioassays using subcutaneous injections, 11 alpha-hydroxyestrone was 2 times as active as 11 alpha-hydroxy-9 beta-estrone, and 11 beta-hydroxyestrone was 10 times as active as 11 beta-hydroxy-9 beta-estrone.
D000818:Animals; D001681:Biological Assay; D004970:Estrone / Q000031:analogs & derivatives*; D005260:Female; D006894:Hydroxyestrones / Q000138:chemical synthesis* / Q000494:pharmacology; D007202:Indicators and Reagents; D007536:Isomerism; D008722:Methods; D051381:Rats; D013329:Structure-Activity Relationship; D014599:Uterus / Q000187:drug effects
D006894:Hydroxyestrones; D007202:Indicators and Reagents; D004970:Estrone; C029971:11-hydroxyestrone