2-Halo derivatives of 3'-acetamido-3'-deoxyadenosine

9-(3-Acetamido-2,5-di-O-acetyl-3-deoxy-beta-D-ribofuranosyl)-2,6-dichloropurine (VI) prepared by the mercuric cyanide catalyzed reaction of 3-acetamido-2,5-di-O-acetyl-3-deoxy-D-ribofuranosyl chloride (III) with 2,6-dichloropurine, was converted by standard reactions to 3'-acetamido-2-chloro-3&...

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Veröffentlicht in:Journal of medicinal chemistry 1975-06, Vol.18 (6), p.571-573
Hauptverfasser: Montgomery, John A, Hewson, Kathleen, Laseter, Anne G
Format: Artikel
Sprache:eng
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Zusammenfassung:9-(3-Acetamido-2,5-di-O-acetyl-3-deoxy-beta-D-ribofuranosyl)-2,6-dichloropurine (VI) prepared by the mercuric cyanide catalyzed reaction of 3-acetamido-2,5-di-O-acetyl-3-deoxy-D-ribofuranosyl chloride (III) with 2,6-dichloropurine, was converted by standard reactions to 3'-acetamido-2-chloro-3'-deoxyadenosine (VII) and 3'-acetamido-3'-deoxy-2-fluoroadenosine (X). The 2-chloroadenine nucleoside VII was not cytotoxic, but the 2-fluoroadenine nucleoside X was moderately so, and its cytotoxicity to a subline of H.Ep.-2 cells resistant to 2-fluoroadenine indicates that its activity is due to the intact nucleoside.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00240a008