Collect. Czech. Chem. Commun.
2005, 70, 479-486
https://doi.org/10.1135/cccc20050479
Synthesis and Estrogenic Activity Screening of Some 6,9-Disubstituted Estradiol Derivatives
Marija N. Sakača,*, Katarina M. Penov Gašia, Mirjana Popsavina, Evgenija A. Djurendića, Silvana Andrićb and Radmila M. Kovačevićb
a Department of Chemistry, Faculty of Sciences, University of Novi Sad, 21000 Novi Sad, Trg Dositeja Obradovića 3, Serbia and Montenegro
b Department of Biology, Faculty of Sciences, University of Novi Sad, 21000 Novi Sad, Trg Dositeja Obradovića 2, Serbia and Montenegro
Abstract
Oxidation of estradiol dipropionate (1) with chromium(VI) oxide-3,5-dimethylpyrazole complex yielded 9α-hydroxy-6-oxoestra-1,3,5(10)-triene-3,17β-diyl dipropionate (2) and 6-oxoestra-1,3,5(10)-triene-3,17β-diyl dipropionate (3). Dehydration of compound 2 with phosphorus(V) oxide or acetic anhydride gave 6-oxoestra-1,3,5(10),9(11)-tetraene-3,17β-diyl dipropionate (5). Reduction of compounds 2 and 5 with sodium borohydride afforded 3,6β,9α-trihydroxyestra-1,3,5(10)-triene-17β-yl propionate (4) and 3,6β-dihydroxyestra-1,3,5(10),9(11)-tetraene-17β-yl propionate (6), respectively. The action of thionyl chloride on compound 2 yielded 6-hydroxyestra-1,3,5(10),6,8-pentaene-3,17β-diyl dipropionate (7). Biological tests in vivo of these compounds showed a moderate antiestrogenic activity of compound 4.
Keywords: Steroids; Estradiol derivatives; Equilenine derivatives; Estrogenic activity; Antiestrogenic activity; Oxidations.
References: 14 live references.
