title: Bioisosters of the diphosphate group in activated forms of antiherpes virus agents. A theoretical study.
abstract: In order to identify potential bioisosteric replacements for the diphosphate moiety, which is present in activated forms generated from antiherpes virus agents during their inhibitory action against herpes viruses, 5'-phosphonoacetamido (4) and 5'-O-sulfamoylcarbamoyl (5) derivatives of idoxuridine were synthesised as analogues of idoxuridine 5'-diphosphate (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 compared with those of the diphosphate metabolite of idoxuridine (6), in order to verify the possibility of bioisosterism relationship between the phosphonoacetamido, the sulfamoylcarbamoyl and the diphosphate group.
authors.affiliation: Istituto di Chimica Farmaceutica e Tossicologica, Università di Pisa, Italy.
authors.forename: M
authors.initials: M
authors.lastname: Macchia
authors.forename: A
authors.initials: A
authors.lastname: Martinelli
authors.forename: A
authors.initials: A
authors.lastname: Parkin
authors.forename: A
authors.initials: A
authors.lastname: Rossello
mesh_terms: D000998:Antiviral Agents / Q000737:chemistry* / Q000494:pharmacology; D002478:Cells, Cultured; D011756:Diphosphates / Q000737:chemistry* / Q000494:pharmacology; D006564:Herpesviridae / Q000187:drug effects*; D007065:Idoxuridine / Q000031:analogs & derivatives; D008958:Models, Molecular; D008962:Models, Theoretical; D008968:Molecular Conformation
chemical_list: D000998:Antiviral Agents; D011756:Diphosphates; D007065:Idoxuridine