Abstract
Iodonium ion mediated cyclization of unsaturated hydroperoxides 1 afforded the expected yingzhaosu A analogues 2. In some cases, however, the corresponding cyclic ethers 5 were formed competitively with the cyclic peroxides 2, the ratios of these two products being a marked function of the structure of the starting materials. Some of the cyclic peroxides 2 showed significant antimalarial activities in vitro and in vivo.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antimalarials / chemical synthesis*
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Antimalarials / pharmacology
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Antimalarials / toxicity
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Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
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Bridged Bicyclo Compounds, Heterocyclic / chemistry*
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Bridged Bicyclo Compounds, Heterocyclic / pharmacology
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Bridged Bicyclo Compounds, Heterocyclic / toxicity
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Catalysis
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Cell Line
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Cyclization
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Malaria / drug therapy
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Mice
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Mice, Inbred ICR
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Onium Compounds
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Peroxides*
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Plasmodium berghei
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Plasmodium falciparum / drug effects
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Pyridines
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Sesquiterpenes*
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Structure-Activity Relationship
Substances
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Antimalarials
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Bridged Bicyclo Compounds, Heterocyclic
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Onium Compounds
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Peroxides
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Pyridines
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Sesquiterpenes
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iodonium dicollidine
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yingzhaosu A