Diethylstilbestrol-linked cytotoxic agents. Synthesis and binding affinity for estrogen receptors
- 1 July 1989
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 32 (7) , 1532-1538
- https://doi.org/10.1021/jm00127a022
Abstract
The syntheses of diethylstilbestrol derivatives with a C4 side chain at the double bond bearing various functional and potentially alkylating groups (9-25, 38-40, 43, 44) as well as the coupling product with daunorubicine (41) are described. Derivatives with free phenolic groups show easy isomerization to (Z)-stilbenes and styrenes, which could be minimized with silyl protecting groups. Estrogen receptor binding is decreased by polar groups such as carboxylic acids (10) as well as sterically demanding substituents.Keywords
This publication has 8 references indexed in Scilit:
- Estrogenic affinity labels: synthesis, irreversible receptor binding, and bioactivity of aziridine-substituted hexestrol derivativesJournal of Medicinal Chemistry, 1987
- Nitrosourea and nitrosocarbamate derivatives of the antiestrogen tamoxifen as potential estrogen receptor-mediated cytotoxic agents in human breast cancer cellsBreast Cancer Research and Treatment, 1986
- Facile geometric isomerization of phenolic non-steroidal estrogens and antiestrogens: Limitations to the interpretation of experiments characterizing the activity of individual isomersThe Journal of Steroid Biochemistry and Molecular Biology, 1985
- Chemically reactive estrogens: synthesis and estrogen receptor interactions of hexestrol ether derivatives and 4-substituted deoxyhexestrol derivatives bearing alkylating functionsJournal of Medicinal Chemistry, 1981
- Potentielle Antineoplastica, III. N‐Lostderivate des Diäthylstilböstrols und des Hexöstrols mit freien phenolischen HydroxylgruppenArchiv der Pharmazie, 1978
- Synthesis of Diethylstilboestrol and Hexoestrol GlucuronidesHoppe-Seyler´s Zeitschrift Für Physiologische Chemie, 1977
- Affinity of estradiol mustard for estrogen receptors and its enzymatic degradation in uterine and breast cancer cytosolsInternational Journal of Cancer, 1976
- Potential Anticancer Agents. II. Urethan-Type Nitrogen Mustards of Some Natural Sex HormonesJournal of Medicinal Chemistry, 1967