Synthesis and Biological Activity of the Nucleoside Analogs Based on Polyfluoroalkyl-Substituted 1,2,3-Triazoles

Abstract

This paper offers the results of a synthesis and study of cytotoxicity and the anti-Epstein-Barr virus (EBV) activity of new 2-deoxy-2-chloro-pyranosyl derivatives of 4-tosyl-5-trifluoromethyl-1,2,3-triazole obtained via the addition reaction of the corresponding 2-N-chlorotriazole to the double bond of 3,4,6-tri-O-acetyl-D-glucal. Nucleoside mimetics, derivatives of 4-tosyl-5-polyfluoroalkyl-1,2,3-triazoles containing fragments of 3-chloro-tetrahydrofuran, 3-chloro-tetrahydropyran, tetrahydropyran, dihydrofuran, dihydropyran, or acyclic substituents, were also studied. Evaluation of cytotoxicity (trypan blue and MTT methods) and anti-EBV activity (polymerase chain reaction (PCR) method) showed high selectivity indices for the compounds 4a, 4b, 5b, 6, and 8. A total of 15 novel compounds were examined in this study.

Keywords:

• Nucleoside analogs
• antiviral agents
• glycals
• Epstein-Barr virus
• 1,2,3-triazole

Notes

- trans diastereoisomer.

- trans diastereoisomer.