Synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure

The acyclic azanucleosides with 2-, 3-, or 4-aminobenzenesulfonyl function at the nitrogen atom of the sugar mimic were prepared by coupling of 2-, 3-, or 4-nitro-N-(2-pivaloyloxyethyl)- N-(pivaloyloxymethyl) benzenesulfonamide with the silylated pyrimidine nucleobases followed by the reduction of the nitro group with sodium dithionite in aqueous solution or the palladium- catalysed transfer hydrogenation. The azanucleosides were evaluated for, but found to be devoid of, activity against several RNA- and DNA-viruses in vitro. (C) 2008 Elsevier Ltd. All rights reserved.