We report the preparation of 2′-alpha-F, 2′-beta-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 beta-fluoro derivative, that retained equal antiviral potency as the parent compound. In contrast, the alpha-fluoro- and 2′,2′-difluoro BCNA derivatives were markedly less (approximately 100-fold) antivirally active.
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