5-Alkylthiomethyl Derivatives of 2'-Deoxyuridine: Synthesis and Antibacterial Activity

摘要

To obtain nucleoside derivatives with antibacterial activity, we have proposed three ways of the synthesis of 5-alkylthiomethyl-2'-deoxyuridines, which was based on the condensation of 3',5'-diacetyl-5-bromomethyl-2'-deoxyuridine with the corresponding 1-mercaptans. 5-Hexylthiomethyl-, 5-octylthiomethyl-, 5-bis(octylthio)methyl-2'-deoxyuridine and alpha and beta anomers of 5-decylthiomethyl-2'-deoxyuridine have been synthesized. The notable cytotoxicity of a number of the synthesized compounds in the A549 cell culture has been shown. 5-Hexylthiomethyl-2'-deoxyuridine has been shown to inhibit the in vitro growth of the Mycobacterium smegmatis mc(2)155 strain with the MIC value of 200 mu g/mL. The other compounds have not inhibited the growth of the Mycobacterium smegmatis and Staphylococcus aureus strains.