Investigations of Nucleoside H-Phosphonamidate in the Design of Nucleotide Prodrug

Abstract

The synthesis, anti-HIV activity and stability studies of a H-phosphonamidate derivative of 3′-azido-2′,3′-dideoxythymidine (AZT) incorporating a N,N-diisopropylamino residue as first model of alkylamino group are reported. The results demonstrate that such phosphorylated structure exerts its biological effects via chemical hydrolysis into the corresponding H-phosphonate, precursor of the parent nucleoside.