RESUMO
Palladium-catalyzed cross-coupling reactions of a 2-substituted 3-iodobenzo[b]furans and stannanyl ester afforded the stereoselective production of 9Z-retinoic acid ester analogs in good yields. These esters were then converted to the corresponding acids via basic hydrolysis in excellent yields, and their biological activities were evaluated. The analog changed the connected position of polyene side chain from 2-position to 3-position of benzo[b]furan decreased the biological activities dramatically, and the introduction of various substituents at 2-position afforded almost no effect on the activities.
Assuntos
Benzofuranos/química , Receptores do Ácido Retinoico/química , Receptores X de Retinoides/química , Tretinoína/síntese química , Tretinoína/farmacologia , Alitretinoína , Animais , Linhagem Celular Tumoral , Humanos , Ligantes , Estrutura Molecular , Ratos , Receptores do Ácido Retinoico/genética , Receptores X de Retinoides/genética , Estereoisomerismo , Relação Estrutura-Atividade , Transcrição Gênica/efeitos dos fármacos , Transcrição Gênica/genética , Ativação Transcricional/efeitos dos fármacos , Tretinoína/químicaRESUMO
A wide variety of 3-iodobenzo[b]furans were readily prepared by iodocyclization of 2-alkynyl-1-(1-ethoxyethoxy)benzenes with the I(coll)2PF6-BF3 x OEt2 combination. Aryl-, vinylic-, and alkyl-substituted alkynes undergo iodocyclization in good to excellent yields. The mechanism of the reaction is also discussed.
