Collect. Czech. Chem. Commun.
2011, 76, 1121-1131
https://doi.org/10.1135/cccc2011074
Published online 2011-08-29 07:53:43
Efficient one-pot synthesis of polysubstituted 6-[(1H-1,2,3-triazol-1-yl)methyl]uracils through the “click” protocol
Petr Jansa*, Petr Špaček, Ivan Votruba, Petra Břehová, Martin Dračínský, Blanka Klepetářová and Zlatko Janeba
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
Abstract
The preparation of several triazolo acyclic nucleosides and triazolo acyclic nucleoside phosphonates is described. The synthetic methodology has been developed as an efficient one-pot Cu(I)-catalyzed azide alkyne Huisgen “click” cycloaddition. A novel Cu(I)-catalyzed decarboxylation reaction of 1-substituted 1H-1,2,3-triazole-4-carboxylic acids at room temperature was observed and used for the preparation of 1-substituted 1H-1,2,3-triazoles. As congeners of TPI (Taiho pharmaceutical inhibitor), the prepared compounds were screened as potential inhibitors of human thymidine phosphorylase, but no inhibitory activity was observed.
Keywords: Nucleosides; Nucleotides; Biological activity; Heterocycles; Phosphorus; Click chemistry.
References: 67 live references.
