Synthesis of Fluorescent C–C Bonded Triazole-Purine Conjugates

A design toward C–C bonded 2,6-bis(1 H -1,2,3-triazol-4-yl)-9 H -purine and 2-piperidinyl-6-(1 H -1,2,3-triazol-4-yl)-9 H -purine derivatives was established using the combination of Mitsunobu, Sonogashira, copper (I) catalyzed azide-alkyne cycloaddition, and S N Ar reactions. 11 examples of 2,6-bis...

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Published in:Journal of fluorescence 2024-05, Vol.34 (3), p.1091-1097
Main Authors: Burcevs, Aleksejs, Sebris, Armands, Traskovskis, Kaspars, Chu, Han-Wei, Chang, Huan-Tsung, Jovaišaitė, Justina, Juršėnas, Saulius, Turks, Māris, Novosjolova, Irina
Format: Article
Language:English
Subjects:
Alkynes
Analytical Chemistry
Animals
Biochemistry
Biological and Medical Physics
Biomedical and Life Sciences
Biomedicine
Biophysics
Biotechnology
Chemical reactions
Conjugates
Cycloaddition
Fluorescence
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Humans
Mice
Molecular Structure
Purines - chemistry
Triazoles
Triazoles - chemistry
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Summary:A design toward C–C bonded 2,6-bis(1 H -1,2,3-triazol-4-yl)-9 H -purine and 2-piperidinyl-6-(1 H -1,2,3-triazol-4-yl)-9 H -purine derivatives was established using the combination of Mitsunobu, Sonogashira, copper (I) catalyzed azide-alkyne cycloaddition, and S N Ar reactions. 11 examples of 2,6-bistriazolylpurine and 14 examples of 2-piperidinyl-6-triazolylpurine intermediates were obtained, in 38–86% and 41–89% yields, respectively. Obtained triazole-purine conjugates expressed good fluorescent properties which were studied in the solution and in the thin layer film for the first time. Quantum yields reached up to 49% in DMSO for bistriazolylpurines and up to 81% in DCM and up to 95% in DMSO for monotriazolylpurines. Performed biological studies in mouse embryo fibroblast, human keratinocyte, and transgenic adenocarcinoma of the mouse prostate cell lines showed that most of obtained triazole-purine conjugates are not cytotoxic. The 50% cytotoxic concentration of the tested derivatives was in the range from 59.6 to 1528.7 µM. Graphical Abstract
ISSN:1053-0509
1573-4994
DOI:10.1007/s10895-023-03337-6