Synthesis and biological profiling of 6- or 7-(het)aryl-7-deazapurine 4'-C-methylribonucleosides
Language English Country England, Great Britain Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
26558518
DOI
10.1016/j.bmc.2015.10.040
PII: S0968-0896(15)30118-8
Knihovny.cz E-resources
- Keywords
- 4′-C-Methyl-ribonucleosides, Branched nucleosides, Nucleoside antivirals, Nucleosides, Prodrugs,
- MeSH
- Antiviral Agents chemical synthesis pharmacology MeSH
- Hepacivirus drug effects MeSH
- Humans MeSH
- Cell Line, Tumor MeSH
- Prodrugs chemical synthesis pharmacology MeSH
- Antineoplastic Agents chemical synthesis pharmacology MeSH
- Purine Nucleosides chemical synthesis pharmacology MeSH
- Purine Nucleotides chemical synthesis pharmacology MeSH
- Dengue Virus drug effects MeSH
- Structure-Activity Relationship MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Antiviral Agents MeSH
- Prodrugs MeSH
- Antineoplastic Agents MeSH
- Purine Nucleosides MeSH
- Purine Nucleotides MeSH
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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