Synthesis and Biological Evaluation of 17-[4-(2-Aminoethoxy)phenyl]-16,17-secoestra-1,3,5(10)-triene Derivatives
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.