Abstract |
1,1,2-Triphenylbut-1-enes (26-35), which are substituted with one or two 3,4-diacetoxy groups or with one 3,4-diacetoxy and one 3- or 4-acetoxy group in two aromatic rings, were synthesized. The occurring E and Z isomers were isolated, and their identity was established by 1H NMR spectroscopy. A study on structure-activity relationship was carried out with regard to estradiol receptor affinity in vitro, estrogenic and antiestrogenic properties in the immature mouse, and inhibition of the hormone-dependent MXT mammary tumor of the mouse in vivo. Among the tested compounds, most of the 1,1-disubstituted 1,1,2-triphenylbut-1-enes (29, Z-30, Z,E-31) and (E)-1-(3-acetoxyphenyl)-1-phenyl-2-(3,4-diacetoxyphenyl)but- 1-ene (E-35) as well as its respective Z isomer (Z-35) exerted antiestrogenic properties. Compounds Z-30, Z,E-31, Z-35, and E-35 inhibited the growth of the hormone-dependent MXT tumor. The best antitumor effect without estrogenic side effects during therapy was shown by E-35.
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Authors | M R Schneider, H Ball, C D Schiller |
Journal | Journal of medicinal chemistry
(J Med Chem)
Vol. 29
Issue 8
Pg. 1355-62
(Aug 1986)
ISSN: 0022-2623 [Print] United States |
PMID | 3016262
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
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Chemical References |
- Alkenes
- Estrogen Antagonists
- Estrogens, Catechol
- Receptors, Estradiol
- Receptors, Estrogen
- 1,1,2-triphenylbut-1-ene
- Diethylstilbestrol
- Cyclofenil
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Topics |
- Alkenes
(metabolism)
- Animals
- Cyclofenil
(pharmacology)
- Diethylstilbestrol
(pharmacology)
- Estrogen Antagonists
(metabolism)
- Estrogens, Catechol
(metabolism)
- Female
- Magnetic Resonance Spectroscopy
- Mammary Neoplasms, Experimental
(drug therapy)
- Mice
- Neoplasm Transplantation
- Receptors, Estradiol
(metabolism)
- Receptors, Estrogen
(metabolism)
- Structure-Activity Relationship
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