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Issue 17, 2007
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Synthesis of 2′-deoxyadenosine nucleosides bearing bipyridine-type ligands and their Ru-complexes in position 8 through cross-coupling reactions

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Abstract

The synthesis of the title 2′-deoxyadenosine derivatives bearing bipyridine, phenanthroline or terpyridine ligands and their corresponding RuII-complexes in position 8 linked viaacetylene 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.

Graphical abstract: Synthesis of 2′-deoxyadenosine nucleosides bearing bipyridine-type ligands and their Ru-complexes in position 8 through cross-coupling reactions

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Article information


Submitted
18 Jun 2007
Accepted
17 Jul 2007
First published
31 Jul 2007

Org. Biomol. Chem., 2007,5, 2849-2857
Article type
Paper

Synthesis of 2′-deoxyadenosine nucleosides bearing bipyridine-type ligands and their Ru-complexes in position 8 through cross-coupling reactions

M. Vrábel, R. Pohl, B. Klepetářová, I. Votruba and M. Hocek, Org. Biomol. Chem., 2007, 5, 2849
DOI: 10.1039/B709245H

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