Synthesis of polyhydroxylated piperidines and evaluation as glycosidase inhibitors.
A series of 16 new chiral nonracemic polyhydroxylated piperidines was synthesized utilizing several chiral beta-amino-alcohols. They act as a nitrogen source, chirality inducer and iminium stabilizer, in the desymmetrization of meso-trihydroxylated glutaraldehyde. The biological activity of these compounds towards several glycosidases (alpha-D-glucosidase, alpha-D-mannosidase, alpha-L-fucosidase) has been evaluated.
Tite
Tony
T
Laboratoire de Pharmacognosie, Faculté des Sciences Pharmaceutiques et Biologiques, UMR 8638 associée au CNRS et à l'Université René Descartes, 4, Avenue de l'Observatoire, 75270 Paris Cedex 06, France.
Lallemand
Marie-Christine
MC
Poupon
Erwan
E
Kunesch
Nicole
N
Tillequin
François
F
Gravier-Pelletier
Christine
C
Le Merrer
Yves
Y
Husson
Henri-Philippe
HP
D001426:Bacterial Proteins / Q000037:antagonists & inhibitors; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D001411:Geobacillus stearothermophilus / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D010880:Piperidines / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D005644:alpha-L-Fucosidase / Q000037:antagonists & inhibitors; D043323:alpha-Mannosidase / Q000037:antagonists & inhibitors
D001426:Bacterial Proteins; D004791:Enzyme Inhibitors; D010880:Piperidines; D006026:Glycoside Hydrolases; D043323:alpha-Mannosidase; D005644:alpha-L-Fucosidase