ArticleBeilstein journal of organic chemistry2019
Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines.
Article in Beilstein journal of organic chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed.
- Purine-based chemical probe with HOMO switching for intracellular detection of mercury ions.Scientific reports · 2025Article
- Synthesis of Purine-1,4,7,10-Tetraazacyclododecane Conjugate and Its Complexation Modes with Copper(II).Molecules (Basel, Switzerland) · 2025Article
- Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization.Molecules (Basel, Switzerland) · 2025Article
- Synthesis of Fluorescent C-C Bonded Triazole-Purine Conjugates.Journal of fluorescence · 2024Article
- Synthesis of 6-Selanyl-2-triazolylpurine Derivatives Using 2,6-Bistriazolylpurines as Starting Materials.ACS omega · 2024Article
- SnAr Reactions of 2,4-Diazidopyrido[3,2-Molecules (Basel, Switzerland) · 2022Article
- Photophysical and Electrical Properties of Highly Luminescent 2/6-Triazolyl-Substituted Push-Pull Purines.ACS omega · 2022Article
- Design and Synthesis of New 5-aryl-4-Arylethynyl-1Molecules (Basel, Switzerland) · 2021Article
- 1,2,3-Triazoles as leaving groups: SBeilstein journal of organic chemistry · 2021Article
- 1,2,3-Triazoles as leaving groups in SBeilstein journal of organic chemistry · 2021Article
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9 authors.
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Abstract
The synthesis of novel fluorescent N(9)-alkylated 2-amino-6-triazolylpurine and 7-deazapurine derivatives is described. A new C(2)-regioselectivity in the nucleophilic aromatic substitution reactions of 9-alkylated-2,6-diazidopurines and 7-deazapurines with secondary amines has been disclosed. The obtained intermediates, 9-alkylated-2-amino-6-azido-(7-deaza)purines, were transformed into the title compounds by CuAAC reaction. The designed compounds belong to the push-pull systems and possess promising fluorescence properties with quantum yields in the range from 28% to 60% in acetonitrile solution. Due to electron-withdrawing properties of purine and 7-deazapurine heterocycles, which were additionally extended by triazole moieties, the compounds with electron-donating groups showed intramolecular charge transfer character (ICT/TICT) of the excited states which was proved by solvatochromic dynamics and supported by DFT calculations. In the 7-deazapurine series this led to increased fluorescence quantum yield (74%) in THF solution. The compounds exhibit low cytotoxicity and as such are useful for the cell labelling studies in the future.
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