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Synthesis and biological profiling of 6- or 7-(het)aryl-7-deazapurine 4'-C-methylribonucleosides
P. Nauš, O. Caletková, P. Perlíková, L. Poštová Slavětínská, E. Tloušťová, J. Hodek, J. Weber, P. Džubák, M. Hajdúch, M. Hocek,
Bioorganic & medicinal chemistry.
2015 ;
23 (23) :
7422-38.
[pub] 20151031
Language English Country England, Great Britain
Document type Journal Article, Research Support, Non-U.S. Gov't
Persistent link
https://www.medvik.cz/link/bmc16027970
- 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
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.
References provided by Crossref.org
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