Synthesis and antimicrobial properties of 5,5′-modified 2′,5′-dideoxyuridines

Abstract

An effective method of synthesis of 5,5′-modified 2′,5′-dideoxyuridine derivatives is based on sequential 5′-iodination and azidation of 5-[4-(1-decyl)-1,2,3-triazol-1-yl]methyl-2′-deoxyuridine followed by 1,3-dipolar cycloaddition of the intermediate azide with an olefin under the catalysis of Cu(I) resulting in 75–85% yield of 5′-[4-substituted (1,2,3-triazol-1-yl]-5-[4-(1-decyl)-1,2,3-triazol-1-yl]methyl-2′,5′-dideoxyuridine. The compounds were shown to possess low cytotoxicity in Vero, A549 cells and Jurkat cell cultures and did not demonstrate noticeable antimicrobial activity.