Add time:08/31/2019 Source:sciencedirect.com
A series of eight N1-(2′-O,4′-C-methylene-β-D-ribofuranonucleoside-3′-yl)-C4-(coumarin-7-oxymethyl)-1,2,3-triazoles have been synthesized by Cu(I)-catalyzed azide-alkyne cycloaddition reaction of 3′-azido-3′-deoxy-2′-O,4′-C-methyleneuridine and 3′-azido-3′-deoxy-2′-O,4′-C-methylene-5-methyluridine with 7-propargyloxy coumarins in 82–88% yields. The synthesized coumarintriazolyl-bicyclonucleoside conjugates possess an extra bridge between 2′-O and 4′-C in the nucleoside moiety, which facilitates its pre-organization into N-type sugar puckering. This was confirmed by X-ray crystal structure studies on one of the conjugates, i.e. on N1-(3′-deoxy-2′-O,4′-C-methylene-5-methyluridin-3′-yl)-C4-(4-phenylcoumarin-7-oxymethyl)-1,2,3-triazole. Photophysical studies carried out on the synthesized compounds demonstrate that they possess useful level of fluorescence with Stokes shift of approximately 70 nm.
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