Abstract
A short synthesis of new beta-1-C-alkyl-1,5-dideoxy-1,5-imino-l-iditols by means of the diastereoselective addition of Grignard reagents onto a glucopyranosylamine is described. These compounds were evaluated as beta-glucocerebrosidase inhibitors and their activity was compared with that of related iminosugar derivatives in the d-gluco and d-xylo series. The results allowed us to conclude on the influence of the hydroxymethyl moiety and of the piperidine-ring conformation on the inhibitory activity.
Copyright 2010 Elsevier Ltd. All rights reserved.
Publication types
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Comparative Study
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkylation
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / pharmacology*
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Glucosylceramidase / antagonists & inhibitors*
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Humans
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Indicators and Reagents
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Kinetics
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Models, Molecular
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Molecular Conformation
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Recombinant Proteins / chemistry
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Spectrometry, Fluorescence
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Stereoisomerism
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Sugar Alcohols / chemical synthesis*
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Sugar Alcohols / pharmacology*
Substances
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Enzyme Inhibitors
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Indicators and Reagents
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Recombinant Proteins
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Sugar Alcohols
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iditol
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Glucosylceramidase