5'-nor carbocyclic ribavirin.
An efficient synthesis of 5'-nor carbocyclic ribavirin (4) is described in 13 steps from conveniently available (+)-(IR,4S)-4-hydroxy-2-cyclopenten-1-yl acetate (6). Compound 4 was evaluated against the following viruses: herpes simplex type 1 and 2, vaccinia, cowpox, smallpox, Ebola, hepatitis B, hepatitis C, adenovirus type 1, influenza A (H1N1 and H3N2), influenza B, parainfluenza type 3, Pichinde, Punta Toro A, respiratory syncytial, rhinovirus type 2, Venezuelan equine encephalitis, yellow fever, and West Nile. No activity was found nor was there any cytotoxicity to the viral host cells.
Tuncbilek
Meral
M
Department of Chemistry, Auburn University, Auburn, Alabama 36849, USA.
Schneller
Stewart W
SW
D000146:Acids, Carbocyclic / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D009705:Nucleosides / Q000138:chemical synthesis / Q000494:pharmacology; D012254:Ribavirin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
C487861:5'-nor carbocyclic ribavirin; D000146:Acids, Carbocyclic; D000998:Antiviral Agents; D009705:Nucleosides; D012254:Ribavirin