title: Synthesis and antiviral evaluation of 4'-alkoxy analogues of 9-(beta-D-xylofuranosyl)adenine.
abstract: BACKGROUND
  Motivated by the reported biological activity of 9-(beta-D-xylofuranosyl)adenine (xylo-A), the synthesis of its 4'-alkoxy analogues was carried out.
  
  
  METHODS
  The starting material 9-(3-deoxy-beta-D-glycero-pento-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 N(6)-pivaloyl derivative (3). When 3 was reacted with meta-chloroperbenzoic acid in the presence of a series of alcohols, the beta-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.
authors.affiliation: School of Pharmaceutical Sciences, Showa University, Tokyo, Japan.
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Kubota
authors.forename: Nobuhide
authors.initials: N
authors.lastname: Ishizaki
authors.forename: Yuri
authors.initials: Y
authors.lastname: Kaneda
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Haraguchi
authors.forename: Yuki
authors.initials: Y
authors.lastname: Odanaka
authors.forename: Hiromichi
authors.initials: H
authors.lastname: Tanaka
authors.forename: Nobuyuki
authors.initials: N
authors.lastname: Kato
authors.forename: Masanori
authors.initials: M
authors.lastname: Baba
authors.forename: Jan
authors.initials: J
authors.lastname: Balzarini
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004267:DNA Viruses / Q000187:drug effects; D012328:RNA Viruses / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000998:Antiviral Agents; C014251:9-xylosyladenine; D000241:Adenosine