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Bioorg Med Chem Lett. 2003 Nov 17;13(22):3963-5.

Synthesis of 2-fluoronoraristeromycin and its inhibitory activity against Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase.

Author information

1
Department of Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido 1-1, Gifu 501-1193, Japan.

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.

PMID:
14592485
DOI:
10.1016/j.bmcl.2003.08.074
[Indexed for MEDLINE]

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