4′-Fluorinated carbocyclic nucleosides: Synthesis and inhibitory activity against S-adenosyl- l-homocysteine hydrolase

4′-Fluorinated analogue of 9-[(1′ R,2′ S,3′ R)-2′,3′-dihydroxy-cyclopentan-1′-yl]adenine (DHCaA) and their related analogues were systematically synthesized under the Mitsunobu and palladium(0) coupling conditions followed by fluorination with inversion of the configuration by using diethylaminosulf...

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Veröffentlicht in:Bioorganic & medicinal chemistry 2006-08, Vol.14 (16), p.5578-5583
Hauptverfasser: Kitade, Yukio, Ando, Takayuki, Yamaguchi, Tsuyoshi, Hori, Ayumi, Nakanishi, Masayuki, Ueno, Yoshihito
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Sprache:eng
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Zusammenfassung:4′-Fluorinated analogue of 9-[(1′ R,2′ S,3′ R)-2′,3′-dihydroxy-cyclopentan-1′-yl]adenine (DHCaA) and their related analogues were systematically synthesized under the Mitsunobu and palladium(0) coupling conditions followed by fluorination with inversion of the configuration by using diethylaminosulfur trifluoride, respectively. 4′-β-Fluoro DHCaA and 2-amino-4′-α-fluoro DHCaA demonstrated slight inhibitory activity against human and Plasmodium falciparum S-adenosyl- l-homocysteine hydrolase, respectively.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2006.04.023