Synthesis of Fluorescent C-C Bonded Triazole-Purine Conjugates

Overview

Journal J Fluoresc

Specialties Biophysics
Chemistry

Date 2023 Jul 17

PMID 37460821

Authors

Aleksejs Burcevs

Armands Sebris

Kaspars Traskovskis

Han-Wei Chu

Huan-Tsung Chang

Justina Jovaisaite

Saulius Jursenas

Maris Turks

Irina Novosjolova

Affiliations

Soon will be listed here.

Abstract

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

Citing Articles

Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization.

Burcevs A, Sebris A, Novosjolova I, Mishnev A, Turks M Molecules. 2025; 30(2).

PMID: 39860206 PMC: 11767399. DOI: 10.3390/molecules30020337.

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