85546-05-0Relevant articles and documents
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.
Isomerization of trans-diethylstilbestrol to pseudo-diethylstilbestrol
Airy, Subbash C.,Sinsheimer, Joseph E.
, p. 593 - 603 (2007/10/02)
This study reports the formation and isolation of a diethylstilbestrol-dimethylsulfoxide (DES-DMSO) adjunct and Z-3,4-di(p-hydroxyphenyl)-2-hexene (ψ-DES) from trans-DES.The presence of ψ-DES was indicated by NMR and mass spectrometry and confirmed by direct comparison to a reference sample.High resolution NMR (360 MHz) along with the comparison of the chemical shift values of methine and methyl protons attached to carbon-carbon double bonds in Z and E isomers of 3-substituted-2-pentenes and dienestrol derivatives were used in postulating the Z-stereochemistry for ψ-DES.A NMR additive increment method was useful for the comparison of the chemical shift values of methine protons in ψ-DES and other literature compounds.Nuclear Overhauser Enhancement (NOE) confirmed the Z-stereochemistry of ψ-DES.