Publication at Faculty of Science |
2015
Abstract
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-beta-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.