Synthesis and biological profiling of 6- or 7-(het)aryl-7-deazapurine 4′-C-methylribonucleosides.

The synthesis and biological activity profiling of a large series of diverse pyrrolo[2,3- d ]pyrimidine 4′- C -methylribonucleosides bearing an (het)aryl group at position 4 or 5 is reported as well as the synthesis of several phosphoramidate prodrugs. These compounds are 4′-C-methyl derivatives of previously reported cytostatic hetaryl-7-deazapurine ribonucleosides. The synthesis is based on glycosylation of halogenated 7-deazapurine bases with 1,2-di- O -acetyl-3,5-di- O -benzyl-4- C -methyl-β- d -ribofuranose followed by cross-coupling and nucleophilic substitution reactions. The final compounds showed low cytotoxicity and several derivatives exerted antiviral activity against HCV or Dengue viruses at micromolar concentrations. [ABSTRACT FROM AUTHOR]