2′-Fluorosugar analogues of the highly potent anti-varicella-zoster virus bicyclic nucleoside analogue (BCNA) Cf 1743

We report the preparation of 2′-α-F, 2′-β-F and 2′,2′-difluoro analogues of the leading anti-varicella zoster virus (VZV) pentylphenyl BCNA Cf 1743. VZV thymidine kinase showed the highest phosphorylating capacity for the β-fluoro derivative, that retained equal antiviral potency as the parent compound. In contrast, the α-fluoro- and 2′,2′-difluoro BCNA derivatives were markedly less (∼100-fold) antivirally active.

Graphical abstractOnly the beta fluoro analogue (X = F, Y = H) retains potent anti-VZV activity.Figure optionsDownload full-size imageDownload as PowerPoint slide