PRODRUGS OF 9-(BETA-D-ARABINOFURANOSYL)ADENINE .2. SYNTHESIS AND EVALUATION OF A NUMBER OF 2',3'-DI-O-ACYL DERIVATIVES AND 3',5'-DI-O-ACYL DERIVATIVES

A number of 2ʹ,3ʹ- and 3ʹ,5ʹ-di-O-acyl derivatives of 9-β-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-β-D-arabinofuranosyl)adenine that was found to be effective as a topical agent in a guinea pig model of genital herpes. © 1979, American Chemical Society. All rights reserved.