TY - JOUR
T1 - Synthesis of 2-fluoronoraristeromycin and its inhibitory activity against Plasmodium falciparum S-Adenosyl-L-homocysteine hydrolase
AU - Kitade, Yukio
AU - Kojima, Hiroharu
AU - Zulfiqur, Fazila
AU - Kim, Hye Sook
AU - Wataya, Yusuke
N1 - Funding Information:
This research was in part supported by Grants-in-Aid for Scientific Research on Priority Areas (KAKENHI 13226034 and 14001072) (to Y.K.) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) and a Grant-in-Aid for JSPS Fellows (to F.Z.) from Japan Society for the Promotion of Science (JSPS).
PY - 2003/11/17
Y1 - 2003/11/17
N2 - 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 (OsO4) in the presence of 4-methylmorpholine N-oxide (NMO) to give 2-fluoronoraristeromycin, possessing significant inhibitory activity against recombinant Plasmodium falciparum SAH hydrolase.
AB - 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 (OsO4) in the presence of 4-methylmorpholine N-oxide (NMO) to give 2-fluoronoraristeromycin, possessing significant inhibitory activity against recombinant Plasmodium falciparum SAH hydrolase.
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U2 - 10.1016/j.bmcl.2003.08.074
DO - 10.1016/j.bmcl.2003.08.074
M3 - Article
C2 - 14592485
AN - SCOPUS:0242365644
VL - 13
SP - 3963
EP - 3965
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
SN - 0960-894X
IS - 22
ER -