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

Yukio Kitade; Hiroharu Kojima; Fazila Zulfiqur; Hye Sook Kim; Yusuke Wataya

doi:10.1016/j.bmcl.2003.08.074

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

Yukio Kitade, Hiroharu Kojima, Fazila Zulfiqur, Hye Sook Kim, Yusuke Wataya

Research output: Contribution to journal › Article › peer-review

41 Citations (Scopus)

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 (OsO₄) in the presence of 4-methylmorpholine N-oxide (NMO) to give 2-fluoronoraristeromycin, possessing significant inhibitory activity against recombinant Plasmodium falciparum SAH hydrolase.

Original language	English
Pages (from-to)	3963-3965
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	13
Issue number	22
DOIs	https://doi.org/10.1016/j.bmcl.2003.08.074
Publication status	Published - Nov 17 2003

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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Synthesis of 2-fluoronoraristeromycin and its inhibitory activity against Plasmodium falciparum S-Adenosyl-L-homocysteine hydrolase. / Kitade, Yukio; Kojima, Hiroharu; Zulfiqur, Fazila; Kim, Hye Sook; Wataya, Yusuke.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 13, No. 22, 17.11.2003, p. 3963-3965.

Research output: Contribution to journal › Article › peer-review

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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 (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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AU - Wataya, Yusuke

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