RESUMEN
Two complementary sets of conditions for radical additions of thiols to terminal ynamides are described. The use of 1 equiv of thiol affords the cis-beta-thioenamide adducts in rapid fashion (10 min) and good dr, whereas employing excess thiol and longer reaction times favors the trans products.
Asunto(s)
Alquinos/química , Péptidos Cíclicos/síntesis química , Compuestos de Sulfhidrilo/química , Tioamidas/síntesis química , Amidas/química , Catálisis , Estructura Molecular , Péptidos Cíclicos/química , Estereoisomerismo , Tioamidas/químicaRESUMEN
4-Arylpyrano-[3,2-c]-pyridones have been prepared by a one-step cyclocondensation of 4-hydroxy-1,6-dimethylpyridin-2(1H)-one with various substituted benzaldehydes and malononitrile. These heterocycles exhibit micromolar and submicromolar antiproliferative activity in HeLa and induce apoptosis in Jurkat cell lines. Structure-activity studies performed on a small library of these compounds show a pronounced cytotoxicity enhancing effect of the bromo substituent at the meta position of the C4 aromatic moiety.