New C2 symmetrical and semisymmetrical substituted imidazolium ribonucleoside. Imidazolic nucleosides analogues

Article abstract of DOI:10.1016/S0957-4166(96)00453-3

New C₂ symmetrical imidazolium ribonucleosides have been synthesized. The silyl Hilbert Johnson-Vorbrugen method was used. Subsequent coupling of trimethylsilylimidazole with the peracylated D-ribofuranose 1, followed by removal of the protecting groups, afforded 1,3-bis(β-D-ribofuranosyl)imidazolium 7 and 1-(β-D-ribofuranosyl)imidazole 8. In a similar synthetic sequence, 4(5)-substituted bis-ribofuranosylimidazolium 14 was also prepared. For the selective preparation of the monoglycosylated imidazole 15, the classical method starting from 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide in acetonitrile and using Hg(CN)₂ was employed. These new base modified nucleosides were devoid of activity, against HIV and cytotoxicity.