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Norbornane-based nucleoside and nucleotide analogues locked in North conformation
M. Dejmek, M. Šála, H. Hřebabecký, M. Dračínský, E. Procházková, D. Chalupská, M. Klíma, P. Plačková, M. Hájek, G. Andrei, L. Naesens, P. Leyssen, J. Neyts, J. Balzarini, E. Boura, R. Nencka,
Bioorganic & medicinal chemistry.
2015 ;
23 (1) :
184-91.
[pub] 20141115
Language English Country England, Great Britain
Document type Journal Article, Research Support, Non-U.S. Gov't
Persistent link
https://www.medvik.cz/link/bmc16000518
- 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
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
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