Synthesis and antiviral evaluation of α-D-2',3'-didehydro-2',3'-dideoxy-3'-C-hydroxymethyl nucleosides.
We have identified a selective S(N)2' reaction triggered by iodide ion that leads to the ring-opening of 2,2'-anhydro-α-nucleosides. By applying the method, we have synthesized α-D-2',3'-didehydro-2',3'-dideoxy-3'-C-hydroxymethyl nucleosides, designed as potential antiviral agents.
Yamada
Kohei
K
Biochemicals Division, Yamasa Corporation, Choshi, Chiba, Japan. k_yamada@yamasa.com
Hayakawa
Hiroyuki
H
Sakata
Shinji
S
Ashida
Noriyuki
N
Yoshimura
Yuichi
Y
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D003587:Cytomegalovirus / Q000187:drug effects; D006678:HIV / Q000187:drug effects; D006801:Humans; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D018139:Simplexvirus / Q000187:drug effects; D014777:Virus Diseases / Q000188:drug therapy; D014780:Viruses / Q000187:drug effects*
D000998:Antiviral Agents; D009705:Nucleosides