Abstract
Adenophorine and its 5-deoxy analogue have been identified as natural iminosugars with efficient glycosidase inhibitory effects. The syntheses and biological evaluation of two new series of 5-deoxyadenophorine analogues in their racemic form are reported. The compounds 12e and 13d bearing a C11 and C7 alkyl chain, respectively, were found to be potent inhibitors of the beta-glucosidase from almond with Ki near to 60 microM. The compounds 13a,d which possess a 3,4-cis stereochemistry were efficient on glucosidases but also on the beta-galactosidase, what was not observed with the 3,4-trans series 12.
Publication types
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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 / chemistry
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Enzyme Inhibitors / pharmacology*
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Galactosidases / antagonists & inhibitors
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Galactosidases / metabolism
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Glucosamine / analogs & derivatives*
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Glucosamine / chemical synthesis
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Glucosamine / chemistry
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Glucosamine / pharmacology
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Glucosidases / antagonists & inhibitors
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Glucosidases / metabolism
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Imino Sugars / chemistry
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Mannosidases / antagonists & inhibitors
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Mannosidases / metabolism
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Molecular Structure
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Structure-Activity Relationship
Substances
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5-deoxyadenophorine
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Enzyme Inhibitors
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Imino Sugars
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Galactosidases
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Glucosidases
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Mannosidases
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Glucosamine