Synthesis and antiviral activity of boranophosphonate isosteres of AZT and d4T monophosphates.
Barral K, Priet S, De Michelis C, Sire J, Neyts J, Balzarini J, Canard B, Alvarez K
We report synthesis, in vitro antiviral activity, and stability studies in biological media of original boranophosphonate isosteres of AZT and d4T monophophates. A convenient route for the synthesis of 3′-Azido-3′-deoxythymidine-5′-boranophosphonate 8 and 2′,3′-Didehydro-3′-dideoxythymidine-5′-boranophosphonate 12 is described. H-phosphinates 7 and 11, and alpha-boranophosphonates 8 and 12 exhibited no significant in vitro activity against HIV-infected cells, neither against a broad panel of viruses, up to 200 microM. The absence of activity of target compounds 8 and 12 can be partially explained by their short half-life in culture medium.Lire l‘article