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. 2024 May;34(3):1091-1097.
doi: 10.1007/s10895-023-03337-6. Epub 2023 Jul 18.

Synthesis of Fluorescent C-C Bonded Triazole-Purine Conjugates

Aleksejs Burcevs  1 , Armands Sebris  1 , Kaspars Traskovskis  2 , Han-Wei Chu  3 , Huan-Tsung Chang  3   4   5   6 , Justina Jovaišaitė  7 , Saulius Juršėnas  7 , Māris Turks  1 , Irina Novosjolova  8
Affiliations

Synthesis of Fluorescent C-C Bonded Triazole-Purine Conjugates

Aleksejs Burcevs et al. J Fluoresc. 2024 May.

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 SNAr 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.

Keywords: CuAAC; Fluorescence; Fluorescent purines; Sonogashira reaction.

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References

    1. Sonogashira K, Tohda Y, Hagihara N (1975) A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines. Tetrahedron Lett 16:4467–4470. https://doi.org/10.1016/S0040-4039(00)91094-3 - DOI
    1. Chinchilla R, Nájera C (2007) The Sonogashira reaction: A booming methodology in synthetic organic chemistry. Chem Rev 107:874–922. https://doi.org/10.1021/cr050992x - DOI - PubMed
    1. Biffis A, Centomo P, Del Zotto A, Zecca M (2018) Pd Metal catalysts for cross-couplings and related reactions in the 21st century: A critical review. Chem Rev 118:2249–2295. https://doi.org/10.1021/acs.chemrev.7b00443 - DOI - PubMed
    1. Johansson Seechurn CCC, Kitching MO, Colacot TJ, Snieckus V (2012) Palladium-catalyzed cross-coupling: A historical contextual perspective to the 2010 nobel prize. Angew Chemie - Int Ed 51:5062–5085. https://doi.org/10.1002/anie.201107017 - DOI
    1. Bag SS, Jana S, Kasula M (2018) Sonogashira cross-coupling: Alkyne-modified nucleosides and their applications. Elsevier Inc

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