Synthesis, in Vitro Antiviral Evaluation, and Stability Studies of Novel α-Borano-Nucleotide Analogues of 9-[2-(Phosphonomethoxy)ethyl]adenine and (R)-9-[2-(Phosphonomethoxy)propyl]adenine

摘要: We describe here the synthesis of 9-[2-(Boranophosphonomethoxy)ethyl]adenine (6a) and (R)-9-[2-(Boranophosphonomethoxy)propyl]adenine (6b), first α-boranophosphonate nucleosides in which a borane (BH3) group substitutes one nonbridging oxygen atom α-phosphonate moiety. H-phosphinates 5a 5b α-boranophosphonates 6a 6b were evaluated for their vitro activity against human immunodeficiency virus (HIV) infected cells panel DNA or RNA viruses. Compounds 5a, 5b, 6a, exhibited no significant antiviral cytotoxicity. To measure chemical enzymatic stabilities target compounds 6b, kinetic data decomposition derivatives standard studied at 37 °C several media. The α-Boranophosphonates metabolized culture medium into with half-live values 5.3 h 1.3 6b.