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.
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.
Robina
I
I
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, E-41071, Sevilla, Spain. pierre.vogel@ico.unil.ch
Moreno-Vargas
A J
AJ
Fernández-Bolaños
J G
JG
Fuentes
J
J
Demange
R
R
Vogel
P
P
D000818:Animals; D002417:Cattle; D015195:Drug Design; D004353:Drug Evaluation, Preclinical; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D004822:Epididymis / Q000201:enzymology; D005260:Female; D005663:Furans / Q000737:chemistry; D020128:Inhibitory Concentration 50; D008297:Male; D010920:Placenta / Q000201:enzymology; D011247:Pregnancy; D005644:alpha-L-Fucosidase / Q000037:antagonists & inhibitors*
D004791:Enzyme Inhibitors; D005663:Furans; D005644:alpha-L-Fucosidase