Synthesis and biological properties of a new series of 5-substituted- pyrimidine-L-nucleoside analogues

Article abstract of DOI:10.1016/S0040-4020(98)00821-7

trans-4-hydroxy-L-proline (5) has been elaborated into a new series of pyrrolidine-L-nucleoside analogues incorporating non-standard 5-substituted- pyrimidine nucleobases, via the azidopyrrolidines 12 and 13. Those analogues employing an acyl protecting group on the primary hydroxyl functionality underwent radical bromination of the ethyl side chain of the pyrimidine ring, to provide E-5-(2-bromovinyl)uracil-pyrrolidine-L-nucleosides 23-26. Of the compounds assessed for potential antiviral activity only 5-ethyluracil- (benzoyloxymethyl)pyrrolidine 20 was found to be a specific inhibitor of vaccinia virus.