155142-81-7Relevant articles and documents
STEROIDS FOR CANCER TREATMENT
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Page/Page column 31, (2010/02/13)
The present invention relates to novel compounds which are 7α-substituted 17-alkylene-16α-hydroxy steroidal estrogens. This invention specifically relates to estrogen derivatives which contain 7α-substituents and which exhibit anti-estrogenic properties. The present invention also relates to use of said compounds as a medicament, and for the treatment of estrogen dependent disorders, a pharmaceutical composition comprising one or more of said compounds and a method of treatment.
Synthesis and estrogenic activity screening of some 6,9-disubstituted estradiol derivatives
Sakac, Marija N.,Penov Gasi, Katarina M.,Popsavin, Mirjana,Djurendic, Evgenija A.,Andric, Silvana,Kovacevic, Radmila M.
, p. 479 - 486 (2007/10/03)
Oxidation of estradiol dipropionate (1) with chromium(VI) oxide-3,5-dimethylpyrazole complex yielded 9α-hydroxy-6-oxoestra-1,3,5(10) -triene-3,17β-diyl dipropionate (2) and 6-oxoestra-1,3,5(10)-triene-3, 17β-diyl dipropionate (3). Dehydration of compound 2 with phosphorus(V) oxide or acetic anhydride gave 6-oxoestra-1,3,5(10),9(11)-tetraene-3,17β- diyl dipropionate (5). Reduction of compounds 2 and 5 with sodium borohydride afforded 3,6β,9α-trihydroxyestra-1,3,5(10)-triene-17β-yl propionate (4) and 3,6β-dihydroxyestra-1,3,5(10),9(11)-tetraene-17β-yl propionate (6), respectively. The action of thionyl chloride on compound 2 yielded 6-hydroxyestra-1,3,5(10),6,8-pentaene-3,17β-diyl dipropionate (7). Biological tests in vivo of these compounds showed a moderate antiestrogenic activity of compound 4.
An expeditious route to 7α-substituted estradiol derivatives
Tedesco, Rosanna,Katzenellenbogen, John A.,Napolitano, Elio
, p. 7997 - 8000 (2007/10/03)
6-Ketoestradiol derivatives are converted in 7α-alkyl substituted estradiol derivatives selectively by alkylation of the generated enolate followed by deoxygenation-deprotection with BF3·Et2O/Et3SiH.
Synthesis and Antiestrogenic Activity of Diaryl Thioether Derivatives
Poirier, Donald,Auger, Serge,Merand, Yves,Simard, Jacques,Labrie, Fernand
, p. 1115 - 1125 (2007/10/02)
The reaction of 1,2-diarylethanol and mercapto side chain catalyzed by ZnI2 was used as a key step in the short (three to five steps) and efficient synthesis of 17 diaryl thioether derivatives.Several of these compounds contain a methyl butyl amide chain and an hydroxyaryl moiety, respectively, for antiestrogenic activity and binding affinity on estrogen receptor.No binding affinity for crude cytosolic preparation of the estrogen receptor was observed for compounds without phenolic group, while a low affinity (0.01-0.05percent) was measured for mono- or diphenol derivatives.Like the pure steroidal antiestrogen EM-139, these novel nonsteroidal compounds did not exert any stimulatory effect on cell proliferation of (ER+) ZR-75-1 human breast cancer cells and partially reversed the amplitude of the stimulatory effect induced by estradiol on this (ER+) cell line.No proliferative or antiproliferative effect on (ER-) MDA-MB-231 human breast cancer cells was also observed for three of these compounds (39-41).Among the newly synthesized nonsteroidal compounds, the thioether derivative 41 (N-butyl-N-methyl-13,14-bis(4'-hydroxyphenyl)-12-thiatetradecanamide), with a long methylbutylalkanamide side chain and a diphenolic nucleus, was selected as the best antiestrogenic compound.However, this compound was 100-fold less antiestrogenic in (ER+) ZR-75-1 cells than the steroidal antiestrogen EM-139.
