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Dec 2010 Organic letters

Ligand-mediated highly effective and selective C-N coupling for synthesizing bioactive N-aryltriazole acyclonucleosides.


Fan Y, Xia Y, Tang J, Rocchi P, Qu F, Iovanna J, Peng L


N-aryltriazole nucleosides are new chemical entities with potential biological activity. The two phosphor ligands, Synphos and Xantphos, had a selective and effective impact on Pd-catalyzed C-N coupling with the 5- and 3-bromotriazole acyclonucleoside isomers, affording the corresponding and otherwise difficult to achieve N-aryltriazole nucleosides with good to excellent yields. In addition, two of the synthesized nucleosides showed superior anticancer activity against drug-resistant pancreatic cancer, compared to the reference drug gemcitabine.

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