title: Synthesis of [(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]-5-methylfuran-4-carboxylic acid derivatives: new leads as selective beta-galactosidase inhibitors.
abstract: The preparation of [(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]furan derivatives in a stereoselective route starting from D-glucose and ethyl acetoacetate is presented. Ethyl ester (6), N,N-diethylamide (7) and N-isopropylamide (8) have been tested towards 25 glycosidases. Ester (6) is a selective inhibitor of beta-galactosidases. The new compounds represent a new type of imino-C-nucleoside analogues.
authors.affiliation: Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, E-41071 Sevilla, Spain.
authors.forename: Antonio J
authors.initials: AJ
authors.lastname: Moreno-Vargas
authors.forename: Raynald
authors.initials: R
authors.lastname: Demange
authors.forename: José
authors.initials: J
authors.lastname: Fuentes
authors.forename: Inmaculada
authors.initials: I
authors.lastname: Robina
authors.forename: Pierre
authors.initials: P
authors.lastname: Vogel
mesh_terms: D000818:Animals; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D005663:Furans / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000494:pharmacology; D013329:Structure-Activity Relationship; D001616:beta-Galactosidase / Q000037:antagonists & inhibitors*
chemical_list: D002264:Carboxylic Acids; D004791:Enzyme Inhibitors; D005663:Furans; D011759:Pyrrolidines; D001616:beta-Galactosidase