Abstract
The unprecedented diastereoselective Mannich reaction of a Z-allylsulfoximine was a key step in the total synthesis of the marine natural products azumamide A and E, and an unnatural analogue. Their relative potency as histone deacetylase inhibitors was evaluated and found to correlate with predicted zinc-binding affinity. [reaction: see text]
Publication types
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Evaluation Study
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Research Support, Non-U.S. Gov't
MeSH terms
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Allyl Compounds / chemistry
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Binding Sites
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Biological Products / chemical synthesis
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Biological Products / pharmacology
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Dapsone / analogs & derivatives
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Dapsone / chemistry
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Drug Design
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / pharmacology
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Histone Deacetylase Inhibitors*
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Models, Chemical
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Peptides, Cyclic / chemical synthesis*
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Peptides, Cyclic / pharmacology
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Stereoisomerism
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Zinc / chemistry
Substances
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Allyl Compounds
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Biological Products
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Enzyme Inhibitors
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Histone Deacetylase Inhibitors
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Peptides, Cyclic
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azumanide A
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azumanide E
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sulfoxone
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Dapsone
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Zinc