1. Synthesis and biological profiling of 6- or 7-(het)aryl-7-deazapurine 4'-C-methylribonucleosides.
- Author
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Nauš P, Caletková O, Perlíková P, Poštová Slavětínská L, Tloušťová E, Hodek J, Weber J, Džubák P, Hajdúch M, and Hocek M
- Subjects
- Antineoplastic Agents chemical synthesis, Antiviral Agents chemical synthesis, Cell Line, Tumor, Dengue Virus drug effects, Hepacivirus drug effects, Humans, Prodrugs chemical synthesis, Purine Nucleosides chemical synthesis, Purine Nucleotides chemical synthesis, Structure-Activity Relationship, Antineoplastic Agents pharmacology, Antiviral Agents pharmacology, Prodrugs pharmacology, Purine Nucleosides pharmacology, Purine Nucleotides pharmacology
- 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-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., (Copyright © 2015 Elsevier Ltd. All rights reserved.)
- Published
- 2015
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