22610-99-7Relevant articles and documents
NON-ESTROGENIC METABOLITES OF DIETHYLSTILBESTROL PRODUCED BY PROSTAGLANDIN SYNTHASE MEDIATED METABOLISM
Degen, Gisela H.,McLachlan, John A.
, p. 253 - 266 (1983)
Incubation of trans-diethylstilbestrol (E-DES) with prostaglandin synthase (PGS) in vitro leads to the formation of the metabolites cis,cis-dienestrol (Z,Z-DIES) and cis-diethylstilbestrol (Z-DES) which have considerably decreased estrogenic activity compared to their parent compound.Incubations of (14C)-E-DES with PGS in the presence of arachidonic acid (AA) predominantly catalyze formation of the oxidative metabolite Z,Z-DIES, accompanied by the formation of protein bound radioactivity.Inhibition of peroxidative metabolism through addition of indomethacin or absence of AA favors isomerization of E-DES to Z-DES without concomitant formation of protein bound radioactivity.Isomerization is inhibited by phenidone (1-phenyl-3-pyrazolidone).Since PGS activity is present in uterine tissue, these pathways may play a role in the metabolism of DES in its target tissue.
Synthesis and biological evaluation of stilbene-based pure estrogen antagonists
Walter, Georg,Liebl, Renate,Von Angerer, Erwin
, p. 4659 - 4663 (2007/10/03)
The nonsteroidal estrogen diethylstilbestrol can be converted into potent antiestrogens devoid of agonist activity by introduction of side chains with appropriate functional groups. Replacement of one of the ethyl substituents in diethylstilbestrol by side chains with functional groups converted this potent estrogen into pure antiestrogens with the potential for the treatment of breast cancer. These agents completely suppressed estrogen receptor-mediated gene activation and inhibited the growth of estrogen-sensitive MCF-7 breast cancer cells in submicromolar concentrations. The most potent derivative displayed similar activity as fulvestrant (ICI 182,780) in vitro and in the mouse uterine weight test. Obviously, the stilbene structure can act as a substitute for estradiol in the development of pure estrogen antagonists.
STERICALLY-DRIVEN ANHYDRIDE FORMATION
Belletire, J. L.,Conroy, G. M.
, p. 403 - 416 (2007/10/02)
Oxidative coupling of highly substituted carboxylic acid dianions affords hindered succinic acid derivatives which undergo facile intramolecular anhydride formation.A novel, but low yield, synthetic sequence converts 4'-methoxypropiophenone into diethylstilbestrol.