title: Synthesis and antiviral activity evaluation of novel 2-phenyl-4-(D-arabino-4'-cycloaminobutyl)triazoles: acyclonucleosides containing unnatural bases.
abstract: Five 2-phenyl-4-(D-arabino-4'-cycloamino-3'-hydroxy-O-1',2'-isopropylidene-butyl)-2H-1,2,3-triazoles, acyclonucleosides containing unnatural bases have been synthesised by opening of the epoxide ring of 2-phenyl-4-(D-arabino-3',4'-epoxy-O-1',2'-isopropylidenebutyl)-2H-1,2,3-triazole with the corresponding cyclic amines in 70-85% yields. The starting arabino-epoxytriazole was prepared in five steps starting from D-glucose in an overall yield of 15%. All the five triazolylacyclonucleosides were unambiguously identified on the basis of their spectral data. The structure of one of the intermediates, that is 2-phenyl-4-(D-arabino-1',2',3',4'-tetrahydroxybutyl)-2H-1,2,3-triazole was confirmed by its X-ray crystallographic studies. These acyclonucleosides were subjected to antiviral activity evaluation in CEM-SS cell-based anti HIV assay with the lymphocytropic virus strains HIV-1(IIIB) and HIV-1(RF).
authors.affiliation: Department of Chemistry, University of Delhi, -110 007, Delhi, India.
authors.lastname: Himanshu
authors.forename: Rahul
authors.initials: R
authors.lastname: Tyagi
authors.forename: Carl E
authors.initials: CE
authors.lastname: Olsen
authors.forename: William
authors.initials: W
authors.lastname: Errington
authors.forename: Virinder S
authors.initials: VS
authors.lastname: Parmar
authors.forename: Ashok K
authors.initials: AK
authors.lastname: Prasad
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001089:Arabinose / Q000138:chemical synthesis* / Q000494:pharmacology; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D018360:Crystallography, X-Ray; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D019380:Anti-HIV Agents; D000998:Antiviral Agents; D014230:Triazoles; D001089:Arabinose