engleski

Sinteza triazolnih derivata 9-deazagvanina kao višenamjenskih proba

Novel derivatives that incorporate 9-deazaguanine linked via a triazole ring to a sugar or amino acid derivatives were synthesized as potential inhibitors of Purine nucleoside phosphorylase (PNP), antitumor agents and highly selective probes for the sensing of nucleic acid secondary structures.Following the most commonly used approach for the formation of the pyrrole ring from pyrimidine, novel 9-deazaguanine (9-DG) derivatives were synthesized and transformed to alkyne derivative by Sonogashira coupling reaction. Copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) between alkyne derivative and ribose or serine derivatives gave 1, 4- disupstituted triazole derivatives, as well as optically active aliphatic 9-DG derivative. The use of click chemistry allows the N-1-substituent of the 1, 2, 3-triazole ring to be easily varied, through the use of different azides, which enables tuning of the electronic and optical properties of the nucleobase analogues.

9-deazaguanine ; click chemistry

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