Synthesis and biological evaluation of ether bridged bicyclic iminosugar derivatives.
ABSTRACT Bicyclic iminosugar derivatives with an ether bridge bearing different substituents on C-2 and the nitrogen atom have been synthesized from a C-glycoside bearing an isopropylidene acetal. The activities of these compounds were investigated against several glycosidase enzymes and showed moderate inhibition and activation.
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ABSTRACT: Two bicyclic iminosugars have been synthesized from polyhydroxylated azepanes by ring isomerization followed by debenzylative cyclization. Their conformations have been studied by NMR and molecular modeling and their glycosidase inhibition profiles were determined. They both adopt a chair conformation for the piperidine ring and display weak inhibition on α-glucosidases.Journal of Carbohydrate Chemistry 01/2012; 30(7-9):641-654. · 0.85 Impact Factor