Abstract
Palladium-coupling reaction of (1S, 4R)-cis-4-acetoxy-2-cyclopenten-1-ol with sodium salt of 2-fluoroadenine resulted in the formation of (1S,4R)-4-(6-amino-2-fluoro-9H-purin-9-yl)cyclopent-2-en-1-ol. Subsequent oxidation was carried out with osmium tetraoxide (OsO(4)) in the presence of 4-methylmorpholine N-oxide (NMO) to give 2-fluoronoraristeromycin, possessing significant inhibitory activity against recombinant Plasmodium falciparum SAH hydrolase.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Adenosine / analogs & derivatives
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Adenosine / chemical synthesis*
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Adenosine / toxicity*
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Adenosylhomocysteinase / antagonists & inhibitors*
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Animals
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Antimalarials / chemical synthesis*
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Antimalarials / pharmacology*
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / pharmacology
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Humans
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Indicators and Reagents
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Kinetics
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Molecular Conformation
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Molecular Structure
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Plasmodium falciparum / enzymology*
Substances
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2-fluoronoraristeromycin
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Antimalarials
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Enzyme Inhibitors
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Indicators and Reagents
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Adenosylhomocysteinase
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Adenosine