Synthesis and antiviral evaluation of 1,4-dioxane nucleoside analogues related to nucleoside dialdehydes.
Since biologically active nucleoside 2',3'-dialdehydes exist as six-membered cyclic acetals (1) in solution, we have investigated the antiviral activity of some structurally similar 1,4-dioxane nucleoside analogues. By reacting 2',3'-seconucleoside tosylates with base, the guanine (10) and adenine (18) substituted (hydroxymethyl)dioxanes have been constructed. In addition, an unusual adenine-substituted divinyl ether (22) was synthesized via a base-catalyzed, double elimination of a 2',3'-di-O-tosyl-2',3'-secoadenosine. None of these compounds showed significant antiviral activity.
D000998:Antiviral Agents / Q000138:chemical synthesis*; D002455:Cell Division; D002460:Cell Line; D004146:Dioxanes / Q000138:chemical synthesis / Q000494:pharmacology; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D010224:Parainfluenza Virus 3, Human / Q000187:drug effects; D018139:Simplexvirus / Q000187:drug effects; D013329:Structure-Activity Relationship; D014616:Vaccinia virus / Q000187:drug effects
D000998:Antiviral Agents; D004146:Dioxanes; D007202:Indicators and Reagents; D009705:Nucleosides