Title: Synthesis and antiviral evaluation of 4'-alkoxy analogues of 9-(beta-D-xylofuranosyl)adenine
Authors: Kubota, Yutaka ×
Ishizaki, Nobuhide
Kaneda, Yuri
Haraguchi, Kazuhiro
Odanaka, Yuki
Tanaka, Hiromichi
Kato, Nobuyuki
Baba, Masanori
Balzarini, Jan #
Issue Date: 2009
Publisher: Blackwell Scientific Publications
Series Title: Antiviral Chemistry & Chemotherapy vol:19 issue:5 pages:201-12
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.
ISSN: 0956-3202
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
× corresponding author
# (joint) last author

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