Abstract
A remarkable increase in antimalarial in vitro activity was achieved by integration of spiroadamantane motifs in 6-alkylidene 1,2,4-trioxanes 3a-h via diastereoselective photooxygenation of allylic alcohols and subsequent BF(3)-catalyzed peroxyacetalization with adamantanone to give the active compounds 3e-h.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Adamantane / chemistry
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Animals
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Antimalarials / chemical synthesis*
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Antimalarials / pharmacology
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Cell Death / drug effects
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Cell Line
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Heterocyclic Compounds / chemical synthesis*
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Heterocyclic Compounds / pharmacology
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Humans
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Inhibitory Concentration 50
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Molecular Structure
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Plasmodium falciparum / drug effects
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Spiro Compounds / chemical synthesis
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Spiro Compounds / pharmacology
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Structure-Activity Relationship
Substances
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Antimalarials
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Heterocyclic Compounds
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Spiro Compounds
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s-trioxane
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Adamantane