Synthesis of 2-fluoronoraristeromycin and its inhibitory activity against Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase.
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.
Kitade
Yukio
Y
Department of Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido 1-1, Gifu 501-1193, Japan.
Kojima
Hiroharu
H
Zulfiqur
Fazila
F
Kim
Hye-Sook
HS
Wataya
Yusuke
Y
D000241:Adenosine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000633:toxicity*; D043383:Adenosylhomocysteinase / Q000037:antagonists & inhibitors*; D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D007202:Indicators and Reagents; D007700:Kinetics; D008968:Molecular Conformation; D015394:Molecular Structure; D010963:Plasmodium falciparum / Q000201:enzymology*
C487476:2-fluoronoraristeromycin; D000962:Antimalarials; D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D043383:Adenosylhomocysteinase; D000241:Adenosine