Pyrimidine acyclic nucleosides. 5-Substituted 1-[(2-aminoethoxy)methyl]uracils as candidate antivirals

Abstract

Several 5-substituted analogues of the acyclic aminonucleoside 1-[2-aminoethoxy)methyl]uracil (5) were prepared for evaluation as antivirals. The uracil and thymine analogues were prepared in two steps from N-[2-(chloromethoxy)ethyl]phthalimide (1). The 5-chloro, 5-bromo, and 5-iodo analogues were prepared by halogenation of 5. These acyclic aminonucleosides exhibited neither cell toxicity nor antiviral activity. This is compatible with their lack of substrate properties toward herpes simplex virus thymidine kinase.