title: 2-Substituted derivatives of 9-alpha-D-arabinofuranosyladenine and 9-alpha-D-arabinofuranosyl-8-azaadenine.
abstract: 2-Substituted derivatives of 9-alpha-D-arabinofuranosyladenine were prepared via the fusion of tetra-O-acetyl-alpha-D-arabinofuranose with 2,6-dichloropurine followed by stepwise displacement of the chloro groups. A different approach, the reaction of 2,3,5-tri-O-benzoly-D-arabinofuranosyl bromide with 2,6-bis(methylthio)-8-azapurine in refluxing toluene in the presence of molecular sieve followed by stepwise reaction of the blocked nucleoside with methanolic ammonia and then other nucleophiles, gave 2-substituted derivatives of 9-alpha-D-arabinofuranosyl-8-azaadenine; In contrast to the parent compounds, none of these 2-substituted derivatives showed significant antiviral activity.
mesh_terms: D000260:Adenoviruses, Human / Q000187:drug effects; D000998:Antiviral Agents / Q000138:chemical synthesis*; D002478:Cells, Cultured; D003587:Cytomegalovirus / Q000187:drug effects; D003588:Cytopathogenic Effect, Viral / Q000187:drug effects; D014645:Herpesvirus 3, Human / Q000187:drug effects; D008722:Methods; D012136:Respiratory Syncytial Viruses / Q000187:drug effects; D012229:Rhinovirus / Q000187:drug effects; D018139:Simplexvirus / Q000187:drug effects; D014740:Vidarabine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: D000998:Antiviral Agents; D014740:Vidarabine