A series of novel 5-(1,2,3-triazolyl)-2′-deoxyuridines were synthesized using a simple
and convenient one-step synthetic procedure via the Huisgen reaction. The key step
in these syntheses is a click reaction at the C-5 position under solvent free microwave
irradiation and CuI as a catalyst. 5-Azidomethyl-2′-deoxyuridine was synthesized from
thymidine and its click reactions with several alkynes provided triazole derivatives
in good yields. The synthesized compounds showed only marginal antiviral activities
[against human rhinovirus (HRV), hepatitis C virus (HCV) and HIV] and antibacterial
activities against a series of Gram positive and Gram negative bacteria. Evaluation
of fluorescence properties of pyrene-modified and EPR studies of nitroxyl spin-labeled
deoxyuridines demonstrate the applicability of these compounds as valuable analytical
tools.
Key words
5-azidomethyl-2′-deoxyuridine - microwave irradiation - click chemistry - EPR - antibacterial
