1H-1,2,3-triazolyl-1,6-naphthyridin-7(6H)-ones as Potential Fluorescent Nucleoside Analogues: Synthesis and Optical Properties - Institut Parisien de Chimie Moléculaire Accéder directement au contenu
Article Dans Une Revue Molecules Année : 2024

1H-1,2,3-triazolyl-1,6-naphthyridin-7(6H)-ones as Potential Fluorescent Nucleoside Analogues: Synthesis and Optical Properties

Résumé

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.

Domaines

Chimie
Fichier principal
Vignette du fichier
molecules-29-00687-v2.pdf (2.57 Mo) Télécharger le fichier
Origine : Fichiers éditeurs autorisés sur une archive ouverte

Dates et versions

hal-04445361 , version 1 (07-02-2024)

Identifiants

Citer

Anissa Beghennou, Océane Rondot, Vincent Corcé, Candice Botuha. 1H-1,2,3-triazolyl-1,6-naphthyridin-7(6H)-ones as Potential Fluorescent Nucleoside Analogues: Synthesis and Optical Properties. Molecules, 2024, Special Issue Nucleoside and Nucleotide Analogues: Chemical Synthesis and Applications, 29 (3), pp.687. ⟨10.3390/molecules29030687⟩. ⟨hal-04445361⟩
36 Consultations
4 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More