Open AccessSynthesis and Antiviral Evaluation of 4'-alkoxy Analogues of 9-(β-D-xylofuranosyl)adenine
Author(s) -
Yutaka Kubota,
Nobuhide Ishizaki,
Yuri Kaneda,
Kazuhiro Haraguchi,
Yuki Odanaka,
Hiromichi Tanaka,
Naoya Kato,
Masanori Baba,
Jan Balzarini
Publication year - 2009
Publication title -
antiviral chemistry and chemotherapy
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.919
H-Index - 51
eISSN - 2040-2066
pISSN - 0956-3202
DOI - 10.1177/095632020901900503
Subject(s) - alkoxy group , chemistry , stereochemistry , pharmacology , biology , organic chemistry , alkyl
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-glycero-pento–3-enofuranosyl)adenine (1) was prepared from adenosine. Compound 1 was converted to the 2',5'-bis-0–(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 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-I) 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-1 from that of xylo-A could be attributable to their inactivity.