Synthesis and biological properties of new stilbene derivatives of resveratrol as new selective aryl hydrocarbon modulators.

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de Medina P, Casper R, Savouret JF, Poirot M

Synthesis and biological properties of new stilbene derivatives of resveratrol as new selective aryl hydrocarbon modulators.

J Med Chem. 2005 Jan 13;48(1):287-91.

PubMed ID

15634023 [ View in PubMed

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Abstract

We developed new stilbene derivatives of resveratrol (E)-1-(4'-hydroxyphenyl)-2-(3,5-dihydroxyphenyl)ethene) selective for AhR and devoid of affinity for ER. Among the 24 stilbenes synthesized, all display a higher affinity than resveratrol for AhR. (E)-1-(4'-Trifluoromethylphenyl)-2-(3,5-ditrifluoromethylphenyl)ethene (4e), (E)-1-(4'-methoxyphenyl)-2-(3,5-dichlorophenyl)ethene (4j), and (E)-1-(4'-chlorophenyl)-2-(3,5-dichlorophenyl)ethene (4b) are selective, high-affinity AhR antagonists with, respective, K(i)s of 2.1, 1.4, and 1.2 nM. (E)-1-(4'-Trifluoromethylphenyl)-2-(3,5-dichlorophenyl)ethene (4i) displays a K(i) of 0.2 nM and is a selective and high-affinity agonist on AhR.

DrugBank Data that Cites this Article

Drug Targets

Drug	Target	Kind	Organism	Pharmacological Action	Actions
Resveratrol	Aryl hydrocarbon receptor	Protein	Humans	Unknown	Not Available	Details

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Resveratrol	Estrogen receptor alpha	Ki (nM)	785	7.4	4	Details