Synthesis and biological evaluation of isonucleosides derived from methyl 3,5-anhydro-2-O-(2-fluorobenzyl)-D-xylofuranosides

Nucleosides Nucleotides Nucleic Acids. 2002;21(3):257-74. doi: 10.1081/ncn-120003290.

Abstract

New isonucleosides [methyl 5-(1-pyrimidinyl)furanosides] are prepared by nucleophilic opening of the oxetane ring of methyl 3,5-anhydro-2-O-(2-fluorobenzyl)-D-xylofuranoside with silylated pyrimidine bases in the presence of trimethylsilyl triflate. Structures, configurations and conformations were determined by NMR techniques and several X-ray diffraction analyses, seven of the isonucleosides were tested for cytotoxicity and activity against HIV, HSV and several other viruses.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-HIV Agents / pharmacology
  • Antiviral Agents / pharmacology
  • Crystallography, X-Ray
  • Furans / chemical synthesis
  • Furans / pharmacology
  • Humans
  • Nucleosides / chemical synthesis*
  • Nucleosides / pharmacology
  • Tumor Cells, Cultured

Substances

  • Anti-HIV Agents
  • Antiviral Agents
  • Furans
  • Nucleosides