Synthesis and biological activity of new 16, 17-secoestrone derivatives

Молимо вас користите овај идентификатор за цитирање или овај линк до ове ставке: https://open.uns.ac.rs/handle/123456789/22890

Назив:	Synthesis and biological activity of new 16, 17-secoestrone derivatives
Аутори:	Jovanović-Šanta Suzana Andric Silvana Kovacevic Radmila Pejanovic V.
Датум издавања:	2000
Часопис:	Collection of Czechoslovak Chemical Communications
Сажетак:	Starting from estrone 3-benzyloxy-17β-hydroxyestra-1,3,5(10)-trien-16-one oxime (3b) was synthesized, which underwent Beckmann fragmentation giving the 3-benzyloxy-17-oxo-16,17-secoestra-1,3,5(10)-triene-16-nitrile (4b). Sodiumb borohydride reduction of this compound afforded 3-benzyloxy-17-hydroxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile (5b). The deprotection of the 3-hydroxy group was achieved by action of hydrogen upon derivatives 4b and 5b in presence of Pd/C as a catalyst, yielding 3-hydroxy-17-oxo-16,17-secoestra-1,3,5(10)-triene-16-nitrile (4a) and 3,17-dihydroxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile (5a). In biological tests on experimental animals, compounds 4a, 4b, 5a and 5b showed virtually a complete loss of estrogenic activity, whereas compounds 4a, 5a and 5b exhibited moderate antiestrogenic effect.
URI:	https://open.uns.ac.rs/handle/123456789/22890
ISSN:	0010-0765 1212-6950
DOI:	10.1135/cccc20000077
Налази се у колекцијама:	PMF Publikacije/Publications