Abstract
Different flavone-, indole-, and furan-17beta-estradiol conjugates, linked via alkyl spacer chains extending from the 17alpha-position of the estradiol moiety, were synthesized by Pd-catalyzed cross-coupling reactions. Structures were assigned based on spectroscopic data. In vitro competitive binding assays for the estrogen receptor (alpha-ER), using [(3)H]estradiol (RBA=100) as a competitor, revealed that a two-carbon alkyl linker combined with a flavone conjugate provided the highest binding affinity (RBA approximately 9), warranting further studies on their potential use as selective estrogen-receptor modulators (SERMs) for hormone-replacement therapies.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Binding, Competitive
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Catalysis
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Estradiol / chemistry*
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Estrogen Receptor alpha / chemistry*
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Estrogen Receptor alpha / drug effects
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Estrogens, Conjugated (USP) / chemical synthesis
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Estrogens, Conjugated (USP) / chemistry*
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Estrogens, Conjugated (USP) / pharmacology
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Flavones / chemistry*
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Furans / chemistry*
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Indoles / chemistry*
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Molecular Structure
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Palladium / chemistry
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Selective Estrogen Receptor Modulators / chemical synthesis
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Selective Estrogen Receptor Modulators / chemistry
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Selective Estrogen Receptor Modulators / pharmacology
Substances
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Estrogen Receptor alpha
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Estrogens, Conjugated (USP)
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Flavones
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Furans
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Indoles
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Selective Estrogen Receptor Modulators
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Estradiol
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Palladium