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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Benzoates* / chemical synthesis
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Benzoates* / chemistry
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Benzoates* / pharmacology
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Binding, Competitive
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Bridged Bicyclo Compounds
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Cycloheptanes
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Dose-Response Relationship, Drug
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Esterification
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Estrogen Receptor alpha
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Estrogens, Non-Steroidal / pharmacology*
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Female
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Ferula / chemistry*
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Humans
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Isoflavones*
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Italy
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Phytoestrogens
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Plant Preparations
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Plants, Medicinal / chemistry*
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Receptors, Estrogen / metabolism*
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Saccharomyces cerevisiae / genetics
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Sesquiterpenes
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Structure-Activity Relationship
Substances
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Benzoates
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Bridged Bicyclo Compounds
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Cycloheptanes
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Estrogen Receptor alpha
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Estrogens, Non-Steroidal
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Isoflavones
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Phytoestrogens
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Plant Preparations
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Receptors, Estrogen
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Sesquiterpenes
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4-oxy-6-(4-oxybezoyloxy)dauc-8,9-en