Norbornane-based nucleoside and nucleotide analogues locked in North conformation
Language English Country England, Great Britain Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
25435471
DOI
10.1016/j.bmc.2014.11.011
PII: S0968-0896(14)00798-6
Knihovny.cz E-resources
- Keywords
- Antiviral, Carbocyclic nucleosides, Norbornane, PI4KIIα, Purines,
- MeSH
- Antiviral Agents chemical synthesis MeSH
- Nucleic Acid Conformation MeSH
- Humans MeSH
- Norbornanes chemical synthesis chemistry MeSH
- Nucleosides chemical synthesis chemistry MeSH
- Nucleotides chemical synthesis chemistry MeSH
- Stereoisomerism MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Antiviral Agents MeSH
- Norbornanes MeSH
- Nucleosides MeSH
- Nucleotides MeSH
We report on the synthesis of novel conformationally locked nucleoside and nucleotide derivatives, which are structurally closely related to clinically used antivirals such as didanosine and abacavir. As a suitable conformationally rigid substitute of the sugar/pseudosugar ring allowing a permanent stabilization of the nucleoside in North conformation we employed bicyclo[2.2.1]heptane (norbornane) substituted in the bridgehead position with a hydroxymethyl group and in the C-3 position with a nucleobase. Prepared nucleoside derivatives were also converted into appropriate phosphoramidate prodrugs (ProTides) in order to increase delivery of the compounds in the cells. All target compounds were evaluated in a broad antiviral and cytostatic assay panel.
References provided by Crossref.org
Purine analogs as phosphatidylinositol 4-kinase IIIβ inhibitors
