3'-Fluoro-3'-deoxy-5'-noraristeromycin derivatives: synthesis and antiviral analysis.
The promising antiviral properties of 3'-fluoro-3'-deoxyadenosine and 4',4'-difluoro-4'-deoxy-5'-noraristeromycin prompted the synthesis of the corresponding 3'-fluoro derivatives of 5'-noraristeromycin. These target compounds, which were prepared from the same readily accessible cyclopentenol, were found to be inactive when subjected to 31 viral assays. The results have some implications on the mechanism of antiviral action of 5'-noraristeromycin and provide guidance for future geminal-difluoro analog design.
Roy
Atanu
A
Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849-5312, USA.
Serbessa
Tesfaye
T
Schneller
Stewart W
SW
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015195:Drug Design; D006801:Humans; D066298:In Vitro Techniques; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship; D014780:Viruses / Q000187:drug effects
D000998:Antiviral Agents; C030034:aristeromycin; D000241:Adenosine