New leads for selective inhibitors of alpha-L-fucosidases. Synthesis and glycosidase inhibitory activities of [(2R,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]furan derivatives

I Robina; A J Moreno-Vargas; J G Fernández-Bolaños; J Fuentes; R Demange; P Vogel

doi:10.1016/s0960-894x(01)00497-8

New leads for selective inhibitors of alpha-L-fucosidases. Synthesis and glycosidase inhibitory activities of [(2R,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]furan derivatives

Bioorg Med Chem Lett. 2001 Sep 17;11(18):2555-9. doi: 10.1016/s0960-894x(01)00497-8.

Authors

I Robina¹, A J Moreno-Vargas, J G Fernández-Bolaños, J Fuentes, R Demange, P Vogel

Affiliation

¹ Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, E-41071, Sevilla, Spain. pierre.vogel@ico.unil.ch

PMID: 11549468
DOI: 10.1016/s0960-894x(01)00497-8

Abstract

Readily derived from D-glucose, 5-[(2R,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]-2-methyl-3-furoic esters and amides are selective and competitive inhibitors (K(i)> or = 3 microM) of alpha-L-fucosidase from bovine epididymis and from human placenta.

Publication types

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

MeSH terms

Animals
Cattle
Drug Design
Drug Evaluation, Preclinical
Enzyme Inhibitors / chemistry*
Enzyme Inhibitors / pharmacology*
Epididymis / enzymology
Female
Furans / chemistry
Inhibitory Concentration 50
Male
Placenta / enzymology
Pregnancy
alpha-L-Fucosidase / antagonists & inhibitors*

Substances

Enzyme Inhibitors
Furans
alpha-L-Fucosidase