Synthesis of tetrazole ribonucleosides and their evaluation as antiviral agents.
Synthesis of 1-beta-D-ribofuranosyltetrazole and two 5-substituted derivatives, i.e., the 5-carboxamide and 5-acetamide, is described. The stereochemical structure of the parent tetrazole ribonucleoside has been established by means of nuclear Overhauser effect and x-ray crystallography. By analogy to the parent compound, the two 5-substituted tetrazole nucleosides are also assigned the beta configuration on the basis of the NMR coupling constant of the anomeric proton and the site of N-ribosylation is determined by 13C NMR studies. Results are also presented on antiviral testing of these synthetic tetrazole nucleosides against influenza A2/Asian/J-305 virus infection in mice.
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000627:therapeutic use; D001393:Azoles / Q000138:chemical synthesis*; D003461:Crystallography; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008958:Models, Molecular; D008968:Molecular Conformation; D009976:Orthomyxoviridae Infections / Q000188:drug therapy; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000627:therapeutic use; D013777:Tetrazoles / Q000138:chemical synthesis* / Q000627:therapeutic use
D000998:Antiviral Agents; D001393:Azoles; D012263:Ribonucleosides; D013777:Tetrazoles