Synthesis of [(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]-5-methylfuran-4-carboxylic acid derivatives: new leads as selective beta-galactosidase inhibitors

Antonio J Moreno-Vargas; Raynald Demange; José Fuentes; Inmaculada Robina; Pierre Vogel

doi:10.1016/s0960-894x(02)00397-9

Synthesis of [(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]-5-methylfuran-4-carboxylic acid derivatives: new leads as selective beta-galactosidase inhibitors

Bioorg Med Chem Lett. 2002 Sep 2;12(17):2335-9. doi: 10.1016/s0960-894x(02)00397-9.

Authors

Antonio J Moreno-Vargas¹, Raynald Demange, José Fuentes, Inmaculada Robina, Pierre Vogel

Affiliation

¹ Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, E-41071 Sevilla, Spain.

PMID: 12161128
DOI: 10.1016/s0960-894x(02)00397-9

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Carboxylic Acids / chemical synthesis
Carboxylic Acids / pharmacology
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / pharmacology
Furans / chemical synthesis
Furans / pharmacology
Humans
Inhibitory Concentration 50
Pyrrolidines / chemical synthesis
Pyrrolidines / pharmacology
Structure-Activity Relationship
beta-Galactosidase / antagonists & inhibitors*

Substances

Carboxylic Acids
Enzyme Inhibitors
Furans
Pyrrolidines
beta-Galactosidase