Synthesis of [(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]-5-methylfuran-4-carboxylic acid derivatives: new leads as selective beta-galactosidase inhibitors.
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.
Moreno-Vargas
Antonio J
AJ
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, E-41071 Sevilla, Spain.
Demange
Raynald
R
Fuentes
José
J
Robina
Inmaculada
I
Vogel
Pierre
P
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*
D002264:Carboxylic Acids; D004791:Enzyme Inhibitors; D005663:Furans; D011759:Pyrrolidines; D001616:beta-Galactosidase