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1H-1,2,3-triazolyl-1,6-naphthyridin-7(6H)-ones as Potential Fluorescent Nucleoside Analogues: Synthesis and Optical Properties
Molecules ( IF 4.2 ) Pub Date : 2024-02-01 , DOI: 10.3390/molecules29030687
Anissa Beghennou 1 , Océane Rondot 1 , Vincent Corcé 1 , Candice Botuha 1
Affiliation  

In this article, we present the synthesis and the optical properties of three original molecules as potential fluorescent ribonucleoside analogues incorporating a 1,6-naphthyridin-7(6H)-one scaffold as a fluorescent nucleobase and a 1,2,3-triazole as a linkage. The nucleosides were prepared via a Cu alkyne-azide cycloaddition (CuAAC) reaction between a ribofuranosyl azide and a 4-ethynylpyridine partner. Construction of substituted 1,6-naphthyridin-7(6H)-ones was achieved through two additional steps. Optical property studies were investigated on nucleoside analogues. Powerful fluorescence properties have been evidenced with a remarkable change of emissivity depending on the polarity of the solvent, making these molecules suitable as a new class of artificial fluorescent nucleosides for investigating enzyme binding sites as well as probing nucleic acids. In addition, we are convinced that such analogues could be of great interest in the search for new antiviral or antitumoral drugs based on nucleosides.

中文翻译:

1H-1,2,3-三唑基-1,6-萘啶-7(6H)-酮作为潜在的荧光核苷类似物:合成和光学性质

在本文中,我们介绍了三种原始分子的合成和光学性质,作为潜在的荧光核糖核苷类似物,其中包含 1,6-naphthyridin-7(6H)-one 支架作为荧光核碱基和 1,2,3-三唑作为一个链接。核苷是通过呋喃核糖基叠氮化物和 4-乙炔基吡啶配偶体之间的 Cu 炔烃叠氮化物环加成 (CuAAC) 反应制备的。通过另外两个步骤构建了取代的 1,6-萘啶-7(6H)-酮。对核苷类似物进行了光学性质研究。强大的荧光特性已被证明具有显着的发射率变化,具体取决于溶剂的极性,使得这些分子适合作为一类新型人工荧光核苷,用于研究酶结合位点以及探测核酸。此外,我们相信,此类类似物对于寻找基于核苷的新型抗病毒或抗肿瘤药物可能会产生极大的兴趣。
更新日期:2024-02-01
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