1. Daucane phytoestrogens: a structure-activity study.
- Author
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Appendino G, Spagliardi P, Cravotto G, Pocock V, and Milligan S
- Subjects
- Binding, Competitive, Bridged Bicyclo Compounds, Cycloheptanes, Dose-Response Relationship, Drug, Esterification, Estrogen Receptor alpha, Female, Humans, Italy, Phytoestrogens, Plant Preparations, Saccharomyces cerevisiae genetics, Sesquiterpenes, Structure-Activity Relationship, Benzoates chemical synthesis, Benzoates chemistry, Benzoates pharmacology, Estrogens, Non-Steroidal pharmacology, Ferula chemistry, Isoflavones, Plants, Medicinal chemistry, Receptors, Estrogen metabolism
- Abstract
The estrogenic activity of a series of analogues of the daucane ester ferutinin (1a) modified at the acyl moiety was investigated in a yeast screen containing the human estrogen receptor alpha. Rather strict structure-activity relationships were observed. Thus, while the parent polyol (jaeschkeanadiol, 2a) was inactive, the presence of a p-hydroxybenzoyl moiety was necessary for activity in the yeast screen. Homologation and vinylation were both detrimental for activity, as were methylation of the p-hydroxyl substituent and the introduction of oxygen functions on the adjacent carbons.
- Published
- 2002
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