Carbocyclic analogues of 5-substituted uracil nucleosides: synthesis and antiviral activity.
Carbocyclic analogues of 3'-deoxyuridines, 3'-deoxyuridines, and uridines with substituents at position 5 of the uracil moiety were prepared by direct halogenation (5-bromo and 5-iodo groups) and by displacement of the 5-bromo group by amino and substituted-amino groups. The analogue of 5-(hydroxymethyl)uridine was prepared via reaction of the isopropylidene derivative of the uridine analogue with paraformaldehyde. The carbocyclic analogues of thymidine and of 5-bromo-, 5-iodo-, and 5-(methylamino)-2'-deoxyuridine were highly active in vitro against herpes simplex virus, types 1 and 2. The corresponding analogues of 5-substituted 3'-deoxyuridines and of 5-substituted uridines were not active in this assay.
D000818:Animals; D000998:Antiviral Agents; D002478:Cells, Cultured; D003857:Deoxyuridine / Q000031:analogs & derivatives*; D007202:Indicators and Reagents; D007668:Kidney; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D011817:Rabbits; D018139:Simplexvirus / Q000187:drug effects; D013329:Structure-Activity Relationship; D014529:Uridine / Q000031:analogs & derivatives*
D000998:Antiviral Agents; D007202:Indicators and Reagents; D009705:Nucleosides; D003857:Deoxyuridine; D014529:Uridine