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

• Published in: Russian journal of bioorganic chemistry Vol. 46; no. 2; pp. 133 - 138
• Main Authors: Negrya, S. D., Makarov, D. A., Solyev, P. N., Karpenko, I. L., Chekhov, O. V., Glukhova, A. A., Vasilyeva, B. F., Sumarukova, I. G., Efremenkova, O. V., Kochetkov, S. N., Alexandrova, L. A.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01.03.2020; Springer Nature B.V
• Subjects: Biochemistry; Biomedical and Life Sciences; Biomedicine; Bioorganic Chemistry; Derivatives; Life Sciences; Organic Chemistry; Penicillin; Synthesis; Thiols; Toxicity; antibacterial activity; 1-mercaptans; nucleosides; radical bromination; cytotoxicity; 5-alkylthiomethyl-2'-deoxyuridines
• ISSN: 1068-1620; 1608-330X
• DOI: 10.1134/S1068162020010070

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 α and β 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 μg/mL. The other compounds have not inhibited the growth of the Mycobacterium smegmatis and Staphylococcus aureus strains.