Prodrugs of 9-(beta-D-arabinofuranosyl)adenine 2. Synthesis and evaluation of a number of 2',3'- and 3',5'-di-O-acyl derivatives.
A number of 2',3'- and 3',5'-di-O-acyl derivatives of 9-beta-D-arabinofuranosyladenine (1) were prepared and evaluated as antivirals. These compounds, designed as prodrugs of 1, offer a range of solubilities and lipophilicities, as well as a resistance to adenosine deaminase, that render some as being attractive as possibly useful antiviral agents. Of particular note is 9-(2,3-di-O-acetyl-beta-D-arabinofuranosyl)adenine that was found to be effective as a topical agent in a guinea pig model of genital herpes.
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis; D055598:Chemical Phenomena; D002621:Chemistry; D005260:Female; D006168:Guinea Pigs; D006561:Herpes Simplex / Q000188:drug therapy; D018139:Simplexvirus / Q000187:drug effects; D014740:Vidarabine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
D000998:Antiviral Agents; D014740:Vidarabine