Artículos de revistas
Synthesis of enantiomeric polyhydroxyalkylpyrrolidines from 1,3-dipolar cycloadducts. Evaluation as inhibitors of a β-galactofuranosidase
Fecha
2016-04Registro en:
Oliveira Udry, Guillermo Alejandro; Repetto, Evangelina; Vega, Daniel Roberto; Varela, Oscar Jose; Synthesis of enantiomeric polyhydroxyalkylpyrrolidines from 1,3-dipolar cycloadducts. Evaluation as inhibitors of a β-galactofuranosidase; American Chemical Society; Journal of Organic Chemistry; 81; 10; 4-2016; 4179-4189
0022-3263
CONICET Digital
CONICET
Autor
Oliveira Udry, Guillermo Alejandro
Repetto, Evangelina
Vega, Daniel Roberto
Varela, Oscar Jose
Resumen
Enantiomeric 2,3,4-tris(hydroxyalkyl)-5-phenylpyrrolidines have been synthesized from the major cycloadducts obtained by the 1,3-dipolar cycloaddition of sugar enones with azomethine ylides derived from natural amino acids. Reduction of the ketone carbonyl group of the cycloadducts, which possess a basic structure of bicyclic 6-(menthyloxy)hexahydropyrano[4,3-c]pyrrol-7(6H)one, afforded a number of pyrrolidine-based bicyclic systems. A sequence of reactions, which involved hydrolysis of the menthyloxy substituent, reduction, N-protection, and degradative oxidation, afforded varied pyrrolidine structures having diverse configurations and patterns of substitution; in particular, polyhydroxylated derivatives have been obtained. The unprotected products were isolated as pyrrolidinium trifluoroacetates. Because of the furanose-like nature of the target trihydroxyalkyl pyrrolidines, these molecules have been evaluated as inhibitors of the β-galactofuranosidase from Penicillium fellutanum. The compounds showed practically no inhibitory activity for concentration of pyrrolidines in the range of 0.1–1.6 mM.