Synthesis and antiviral evaluation of 4′-alkoxy analogues of 9-(β-D-xylofuranosyl)adenine

Yutaka Kubota, Nobuhide Ishizaki, Yuri Koneda, Kozuhiro Haroguchi, Yuki Odanoko, Hiromichi Tanaka, Nobuyuki Kato, Masanori Baba, Jan Balzarini

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)


Background: Motivated by the reported biological activity of 9-(β-D-xylofuranosyl)adenine (xylo-A), the synthesis of its 4′-alkoxy analogues was carried out. Methods: The starting material 9-(3-deoxy-β-D-glyceropento-3-enofuranosyl)adenine (1) was prepared from adenosine. Compound 1 was converted to the 2′,5′-bis-O-(tert-butyldimethylsilyl) derivative (2) and then to the N6-pivaloyl derivative (3). When 3 was reacted with meta-chloroperbenzoic acid in the presence of a series of alcohols, the β-D-isomer of the respective 4′-alkoxy derivative was obtained exclusively in high yield. Deprotection of these products led to the isolation of the desired 4′ alkoxy analogues (8a-l) of xylo-A. Results: Antiviral evaluation revealed that none of these analogues showed inhibitory activity against a wide variety of DNA and RNA viruses. Conclusions: We assume that conformational difference of the sugar moiety of 8a-l from that of xylo-A could be attributable to their inactivity.

Original languageEnglish
Pages (from-to)201-212
Number of pages12
JournalAntiviral Chemistry and Chemotherapy
Issue number5
Publication statusPublished - 2008
Externally publishedYes

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Virology


Dive into the research topics of 'Synthesis and antiviral evaluation of 4′-alkoxy analogues of 9-(β-D-xylofuranosyl)adenine'. Together they form a unique fingerprint.

Cite this