Synthesis and antiviral evaluation of 4'-alkoxy analogues of 9-(beta-D-xylofuranosyl)adenine.
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.
Kubota
Yutaka
Y
School of Pharmaceutical Sciences, Showa University, Tokyo, Japan.
Ishizaki
Nobuhide
N
Kaneda
Yuri
Y
Haraguchi
Kazuhiro
K
Odanaka
Yuki
Y
Tanaka
Hiromichi
H
Kato
Nobuyuki
N
Baba
Masanori
M
Balzarini
Jan
J
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
D000998:Antiviral Agents; C014251:9-xylosyladenine; D000241:Adenosine