Nucleic Acid Related Compounds. 47. Synthesis and Biological Activities of Pyrimidine and Purine "Acyclic" Nucleoside Analogues

Article abstract of DOI:10.1021/jm00377a018

Various acyclic, i.e., (2-hydroxyethoxy)methyl and (2-acetoxyethoxy)methyl, analogues of pyrimidine and purine nucleosides have been prepared evaluated for their antiviral, antimetabolic, and cytotoxic properties.All of the pyrimidine analogues, including (E)-5-(2-bromovinyl)-1-<(2-hydroxyethoxy)methyl>uracil (12) and its O-acetyl derivative (13), were virtually devoid of antiviral, cytotoxic, and antimetabolic activities.However, several of the 8-substituted derivatives of 9-<(2-hydroxyethoxy)methyl>guanine (acyclovir) had higher antiviral specificity in vitro than the parent drug.The 8-methyl-, 8-amino-, 8-bromo-, and 8-iodoacyclovir derivatives have activities worthy of further investigation.