Synthesis of 2'-deoxyadenosine nucleosides bearing bipyridine-type ligands and their Ru-complexes in position 8 through cross-coupling reactions
Language English Country Great Britain, England Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
17700854
DOI
10.1039/b709245h
Knihovny.cz E-resources
- MeSH
- Antiviral Agents chemical synthesis chemistry toxicity MeSH
- Deoxyadenosines chemical synthesis chemistry toxicity MeSH
- X-Ray Diffraction MeSH
- Hepacivirus drug effects MeSH
- Ligands MeSH
- Models, Molecular MeSH
- Molecular Structure MeSH
- Antineoplastic Agents chemical synthesis chemistry toxicity MeSH
- Pyridines chemistry MeSH
- Cross-Linking Reagents chemistry MeSH
- Ruthenium Compounds chemistry MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- 2'-deoxyadenosine MeSH Browser
- Antiviral Agents MeSH
- Deoxyadenosines MeSH
- Ligands MeSH
- Antineoplastic Agents MeSH
- Pyridines MeSH
- Cross-Linking Reagents MeSH
- Ruthenium Compounds MeSH
The synthesis of the title 2'-deoxyadenosine derivatives bearing bipyridine, phenanthroline or terpyridine ligands and their corresponding RuII-complexes in position 8 linked via acetylene or phenylene tethers was accomplished through cross-coupling reactions. The Suzuki-Miyaura reactions of boronic acids or the Sonogashira reactions of terminal acetylene derivatives of oligopyridine ligands were performed either on protected 8-bromoadenosines in organic solvents or, more efficiently, directly on unprotected nucleosides in aqueous acetonitrile or DMF. Direct cross-coupling reactions of unprotected nucleosides with RuII-complexes or the oligopyridine-boronic acids or -acetylenes gave the Ru-labelled nucleosides in one step in fair to good yields. This method was also proven to be applicable for direct Ru-labelling of dATP. Terpyridine-containing 2'-deoxyadenosine exerted significant antiviral and cytostatic effects.
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