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

✍ Scribed by A. Al Mourabit; M. Beckmann; C. Poupat; A. Ahond; P. Potier

• Book ID: 104360912
• Publisher: Elsevier Science
• Year: 1996
• Tongue: English
• Weight: 626 KB
• Volume: 7
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(96)00453-3

✦ Synopsis

New C2 symmetrical imidazolium ribonucleosides have been synthesized. The silyl Hilbert Johnson-Vorbr0gen method was used. Subsequent coupling of trimethylsilylimidazole with the peracylated D-ribofuranose 1, followed by removal of the protecting groups, afforded 1,3-bis(13-D -ribofuranosyl)imidazolium 7 and 1-(13-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.