Highly potent naphthofuran-based retinoic acid receptor agonists.
Fiche publication
Date publication
mai 2009
Auteurs
Membres identifiés du Cancéropôle Est :
Dr GRONEMEYER Hinrich
Tous les auteurs :
Santin EP, Khanwalkar H, Voegel J, Collette P, Mauvais P, Gronemeyer H, de Lera AR
Lien Pubmed
Résumé
A collection of arotinoids with a central benzofuran or naphthofuran ring structure was efficiently synthesized by a three-step process that comprises a Sonogashira coupling, an iodine-induced 5-endo-dig cyclization of the o-methoxyphenyl- or naphthyl-ethynyl benzoates, and finally a Suzuki/Sonogashira coupling of the corresponding 3-iodobenzo- or naphthofurans. Most of these 3-substituted naphthofuran arotinoids (but not the 5,7-di-tert-butylbenzofurans with the same substitution pattern at the C2 and C3 positions) are potent agonists of the retinoic acid receptor (RAR) subtypes, with activities in the nanomolar range.
Référence
ChemMedChem. 2009 May;4(5):780-91.