BIOISOSTERS OF THE DIPHOSPHATE GROUP IN ACTIVATED FORMS OF ANTIHERPESVIRUS AGENTS - A THEORETICAL-STUDY

In order to identify potential bioisosteric replacements for the dipho sphate moiety, which is present in activated forms generated from anti herpes virus agents during their inhibitory action against herpes viru ses, 5'-phosphonoacetamido (4) and 5'-O-sulfamoylcarbamoyl (5) derivat ives of idoxuridine were synthesised as analogues of idoxuridine 5'-di phosphate (6). In this paper we report on the antiherpetic activity of 4 and 5. Moreover, a theoretical study is presented in which both the conformational and the electronic characteristics of 4 and 5 are comp ared with those of the diphosphate metabolite of idoxuridine (6), in o rder to verify the possibility of bioisosterism relationship between t he phosphonoacetamido, the sulfamoylcarbamoyl and the diphosphate grou p.