Synthesis and biological evaluation of 9-[2-fluoro-4-hydroxy-3-hydroxymethyl-2-butenyl]adenine and its related compounds as open-chain analogues of neplanocin A

Novel 9-[2-fluoro-4-hydroxy-3-hydroxymethyl-2-butenyl]adenine and its related compounds were designed and synthesized as open-chain analogues of neplanocin A. Alkylation of adenine or pyrimidine bases with the mesylate4 was chosen as a simple approach to the synthesis of 2-fluoro-2-butenylated nucleosides. Mesylate4 was prepared from dihydroxyacetone dimervia four steps in 58% overall yield. The synthesized compounds were evaluated their antiviral activity against HSV, HIV and Polio viruses.