Abstract
A solid-phase synthesis of new N-substituted valienamines has been developed and new synthesis of (+/-)-conduramine F-1, (-)-conduramine F-1, and (+)-ent-conduramine F-1 is presented, together with the preparation of N-benzylated conduramines F-1. N-Benzylation of both valienamine and (+)-ent-conduramine F-1 improves their inhibitory activity toward alpha-glucosidases significantly. The additional hydroxymethyl group makes valienamine derivatives more active than their (+)-ent-conduramine F-1 analogues.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Cyclohexanols / chemical synthesis
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Cyclohexanols / chemistry
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Cyclohexanols / pharmacology*
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Cyclohexenes
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Cyclohexylamines / chemical synthesis
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Cyclohexylamines / chemistry
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Cyclohexylamines / pharmacology*
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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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Glycoside Hydrolase Inhibitors*
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Hexosamines / chemical synthesis
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Hexosamines / chemistry
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Hexosamines / pharmacology*
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Molecular Structure
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Stereoisomerism
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Structure-Activity Relationship
Substances
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6-aminocyclohex-4-ene-1,2,3-triol
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Cyclohexanols
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Cyclohexenes
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Cyclohexylamines
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Enzyme Inhibitors
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Glycoside Hydrolase Inhibitors
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Hexosamines
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valienamine