Synthesis and biological activities of new heterocyclic aromatic retinoids

A series of 3-aryl-2H-1-benzopyrancarboxylic acid derivatives was synthesized and evaluated as Retinoic Acid Receptor (RAR) agonists. By modifications of the 3-aryl group, we have obtained new retinoids exhibiting potent cellular differentiating activities and high affinities for RARs. Moreover, hydrogenation of the 2H-1-benzopyran ring led to the 3-(5,6,7,8-tetrahydro-5,5,8,8,-tetramethyl-naphthalen-2-yl)-3,4-dihydro-2H-1-benzopyran-7-yl carboxylic acid, characterized by a RARß binding profile.