Synthesis and evaluation as glycosidase inhibitors of 2,5-imino-D-glucitol and 1,5-imino-D-mannitol related derivatives.
Selectively functionalized 2,5-imino-D-glucitol and 1,5-imino-D-mannitol derivatives were synthesized and tested as precursors of hydrolytically resistant pseudo-disaccharides. Among them N-acetyl-6-amino-6-deoxy-2,5-imino-D-glucitol (11) and N-acetyl-6-amino-6-deoxy-1,5-imino-D-mannitol (12) were found potent and specific inhibitors against beta-D-glucosidase and alpha-L-fucosidase, respectively.
McCort
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I
University René Descartes, Laboratoire e Chimie et Biochimie Pharmacologiques et Toxicologiques, associé au CNRS, Paris, France. mccort@biomedicale.univ-paris5.fr
Fort
S
S
Duréault
A
A
Depezay
J C
JC
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D005069:Evaluation Studies as Topic; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D009682:Magnetic Resonance Spectroscopy; D008353:Mannitol / Q000031:analogs & derivatives* / Q000494:pharmacology; D013058:Mass Spectrometry; D013012:Sorbitol / Q000031:analogs & derivatives* / Q000494:pharmacology; D005644:alpha-L-Fucosidase / Q000037:antagonists & inhibitors*
D004791:Enzyme Inhibitors; D008353:Mannitol; D013012:Sorbitol; D006026:Glycoside Hydrolases; D005644:alpha-L-Fucosidase