A facile synthesis of 4'-thio-arabinonucleosides as potential antiviral agents from D-glucose.
As potential antiviral agents, 4'-thio-arabinonucleosides were synthesized. Methyl 3-O-benzyl-xylo-furanoside, readily obtained from D-glucose, was converted to 1,4-anhydro-4-deoxy-4-thio-arabinitol. The protection of hydroxyl groups and the Pummerer rearrangement, followed by Lewis acid induced glycosylation afforded 4'-thio-arabinonucleosides. The compounds showed anti HSV-1 activity.
Yoshimura
Y
Y
Research and Development Division, Yamasa Corporation, Chiba, Japan.
Watanabe
M
M
Sakata
S
S
Ashida
N
N
Miyazaki
S
S
Machida
H
H
Matsuda
A
A
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001087:Arabinonucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015195:Drug Design; D006031:Glycosylation; D018259:Herpesvirus 1, Human / Q000187:drug effects; D018258:Herpesvirus 2, Human / Q000187:drug effects; D014645:Herpesvirus 3, Human / Q000187:drug effects; D015394:Molecular Structure; D013872:Thionucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000998:Antiviral Agents; D001087:Arabinonucleosides; D013872:Thionucleosides