title: Ribavirin derivatives with a hexitol moiety: synthesis and antiviral evaluation.
abstract: Current standard therapy for the treatment of chronic infections with hepatitis C virus consists of combination therapy with (pegylated) interferon-alpha and ribavirin. 1,5-Anhydrohexitol nucleoside analogues are constrained congeners known to mimic the ribonucleoside conformation. Within this series some analogues are endowed with strong antiviral properties, particularly against herpesviruses. The six-membered anhydrohexitol ring was, therefore, combined with the triazolyl carboxamide moiety of ribavirin, thus providing a new series of ribavirin analogues. None of the newly synthesized compounds elicited any substantial antiviral activity, neither against herpes simplex virus type 1 and 2, nor against bovine viral diarrhoea virus (a surrogate for hepatitis C virus) or the yellow fever virus.
authors.affiliation: Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, Katholieke Universiteit Leuven, Leuven, Belgium. Arthur.VanAerschot@REGA.KULeuven.ac.be
authors.forename: Arthur
authors.initials: A
authors.lastname: Van Aerschot
authors.forename: Guy
authors.initials: G
authors.lastname: Schepers
authors.forename: Roger
authors.initials: R
authors.lastname: Busson
authors.forename: Jef
authors.initials: J
authors.lastname: Rozenski
authors.forename: Johan
authors.initials: J
authors.lastname: Neyts
authors.forename: Erik
authors.initials: E
authors.lastname: De Clercq
authors.forename: Piet
authors.initials: P
authors.lastname: Herdewijn
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002460:Cell Line; D001908:Diarrhea Viruses, Bovine Viral / Q000187:drug effects / Q000254:growth & development; D006564:Herpesviridae / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008956:Models, Chemical; D012254:Ribavirin / Q000031:analogs & derivatives* / Q000494:pharmacology; D013402:Sugar Alcohols / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry; D015005:Yellow fever virus / Q000187:drug effects / Q000254:growth & development
chemical_list: D000998:Antiviral Agents; D013402:Sugar Alcohols; D014230:Triazoles; D012254:Ribavirin