title: 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.
authors.affiliation: Institute of Organic Chemistry NAS of Ukraine, Kyiv, Ukraine.
authors.forename: Oleksandr S
authors.initials: OS
authors.lastname: Kanishchev
authors.forename: Ganna P
authors.initials: GP
authors.lastname: Gudz
authors.forename: Yuriy G
authors.initials: YG
authors.lastname: Shermolovich
authors.forename: Nadezhda V
authors.initials: NV
authors.lastname: Nesterova
authors.forename: Svetlana D
authors.initials: SD
authors.lastname: Zagorodnya
authors.forename: Anna V
authors.initials: AV
authors.lastname: Golovan
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D003587:Cytomegalovirus / Q000187:drug effects; D003847:Deoxyglucose / Q000031:analogs & derivatives / Q000737:chemistry; D004854:Herpesvirus 4, Human / Q000187:drug effects*; D006801:Humans; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014105:Tosyl Compounds / Q000494:pharmacology*; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000998:Antiviral Agents; D009705:Nucleosides; D014105:Tosyl Compounds; D014230:Triazoles; C043334:3,4,6-tri-O-acetylglucal; D003847:Deoxyglucose