Synthesis and Biological Profiling of 6- or 7-(Het)aryl-7-deazapurine 4’-C-Methylribonucleosides

Publication date: Available online 31 October 2015
Source:Bioorganic & Medicinal Chemistry
Author(s): Petr Nauš, Olga Caletková, Pavla Perlíková, Lenka Poštová Slavětínská, Eva Tloušťová, Jan Hodek, Jan Weber, Petr Džubák, Marián Hajdúch, Michal Hocek
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.

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