Journal
JOURNAL OF COMBINATORIAL CHEMISTRY
Volume 10, Issue 6, Pages 981-985Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cc8001475
Keywords
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Funding
- Ministry of Higher Education, Science and Technology of the Republic of Slovenia
- Slovenian Research Agency [PI-02300103]
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Azoamides, previously established as bioactive intracellular GSH-depleting agents, were decorated with a terminal alkyne moiety to 4 and then were transformed, bycopper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), into different ligand-arm functionalized azoamides 6. Azides 5 having ligand-arms amenable for binding to platinum(II) were selected for this study. Because, for the fragile azoamides 4, the typically employed reaction conditions for CuAAC failed, several alternative solvents and copper catalysts were tested. Excellent results were obtained with copper(II) sulfate pentahydrate/metallic copper and especially with heterogeneous catalysts, such as copper-in-charcoal, cupric oxide, and cuprous oxide. The heterogeneous catalysts were employed to obtain the desired products in almost quantitative yields by a simple three-step stir-filter-evaporate protocol with no or negligible contamination with copper impurities. This is of particular importance because compounds 6 have been designed for coordination.
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