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Highly Potent Naphthofuran‐Based Retinoic Acid Receptor Agonists
Author(s) -
Santín Efrén Pérez,
Khanwalkar Harshal,
Voegel Johannes,
Collette Pascal,
Mauvais Pascale,
Gronemeyer Hinrich,
de Lera Ángel R.
Publication year - 2009
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.200900015
Subject(s) - retinoic acid receptor , retinoic acid , chemistry , pharmacology , agonist , retinoic acid receptor gamma , retinoic acid receptor beta , receptor , retinoid x receptor gamma , retinoic acid receptor alpha , biochemistry , biology , gene
A series of arotinoids with a central benzofuran or naphthofuran ring structure were synthesized by an efficient three‐step process. Most of these 3‐substituted naphthofuran arotinoids are potent agonists of the retinoic acid receptor (RAR) subtypes, with activities in the nanomolar range.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.