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

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.
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https://www.hal.inserm.fr/inserm-00090771
Contributor : Marc Poirot Connect in order to contact the contributor
Submitted on : Saturday, September 2, 2006 - 11:39:36 PM
Last modification on : Monday, July 4, 2022 - 9:22:14 AM

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Philippe de Médina, Robert Casper, Jean-François Savouret, Marc E. Poirot. Synthesis and biological properties of new stilbene derivatives of resveratrol as new selective aryl hydrocarbon modulators.. Journal of Medicinal Chemistry, American Chemical Society, 2005, 48, pp.287-91. ⟨10.1021/jm0498194⟩. ⟨inserm-00090771⟩

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