Synthesis of Novel 6-Azapyrimidine Acyclic Nucleoside Analogues and Antiviral Evaluation

Abstract

Acyclic nucleosides have been of considerable interest since the approval of aciclovir by the FDA to be used as an antiviral agent in the 1990s. The acyclic moieties and the bases used in the experiment were either available commercially or synthesized using literature methods. Vorbrüggen coupling method was utilized involving reaction of persilylated heterocyclic bases with the appropriate acyclic moiety in the presence of a Lewis acid catalyst. A series of novel 6-azapyrimidine acyclic oxosugar nucleosides was successfully synthesized with a promising yield (more than 50%). An efficient method of protection and deprotection was also investigated.

Keywords:

• Antiviral
• 6-azapyrimidine acyclic nucleosides
• coupling
• deprotection

Acknowledgments

M.J. acknowledges the Malaysian Government for research funding.