Collect. Czech. Chem. Commun.
2007, 72, 403-410
https://doi.org/10.1135/cccc20070403
Synthesis and Biological Evaluation of 17-[4-(2-Aminoethoxy)phenyl]-16,17-secoestra-1,3,5(10)-triene Derivatives
Marija N. Sakača,*, Katarina M. Penov Gašia, Evgenija A. Djurendića, Silvana Andrićb and Dušan A. Miljkovića
a Department of Chemistry, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 3, 21000 Novi Sad, Serbia
b Department of Biology, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 2, 21000 Novi Sad, Serbia
Abstract
Starting from 3-(benzyloxy)-16-(hydroxyimino)estra-1,3,5(10)-trien-17-one (1), 3-(benzyloxy)- 17-{4-[2-(dimethylamino)ethoxy]phenyl}-17-oxo-16,17-secoestra-1,3,5(10)-triene-16-nitrile (3a) was synthesized. Reduction of 3a with sodium borohydride yielded secocyano alcohol 4a, as well as the secoamino alcohol 5a when reduction was performed with sodium borohydride in the presence of cobalt(II) salt. Deprotection of the C-3 hydroxy group in compounds 3a-5a by catalytic hydrogenolysis resulted in the corresponding 3-hydroxy derivatives 3b-5b. Compounds 3b-5b were tested on residual estrogenic and potential antiestrogenic activities.
Keywords: Steroids; 16,17-Secosteroids; Estra-1,3,5(10)-triene derivatives; Nitriles; Estrogenic activity; Antiestrogenic activity.
References: 10 live references.
