Synthesis and Photophysical Studies on N1-(2'-O,4'-C-Methyleneribofurano-nucleoside-3'-yl)-C4-(coumarin-7-oxymethyl)-1,2,3-triazoles

Abstract

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.