title: Design and synthesis of DNA-intercalating 9-fluoren-beta-O-glycosides as potential IFN-inducers, and antiviral and cytostatic agents.
abstract: Novel 9-fluoren-beta-O-glycosides, designed as DNA-intercalating agents in structural correlation with antiviral tilorone and anticancer anthracyclines, have been prepared with yields in beta-anomers ranging between 25 and 63%. They have been screened for antiproliferative, immunostimulating and antiviral properties against HSV-1 and HSV-2 viruses. Compounds displaying significant antiviral activity against HSV-2 are acetylated 1 and deprotected 6 9-fluorenyl-O-d-arabinopyranoses, whereas 9-fluorenyl-O-d-glucopyranose 3 is the most effective on HSV-1 replication, followed by 1 and 6. The conformational properties of these compounds have been evaluated by molecular modelling techniques.
authors.affiliation: Dipartimento di Scienze Farmacobiologiche, Università di Catanzaro 'Magna Graecia', Complesso Ninì Barbieri - 88021 Roccelletta di Borgia (CZ), Italy.
authors.forename: S
authors.initials: S
authors.lastname: Alcaro
authors.forename: A
authors.initials: A
authors.lastname: Arena
authors.forename: S
authors.initials: S
authors.lastname: Neri
authors.forename: R
authors.initials: R
authors.lastname: Ottanà
authors.forename: F
authors.initials: F
authors.lastname: Ortuso
authors.forename: B
authors.initials: B
authors.lastname: Pavone
authors.forename: M G
authors.initials: MG
authors.lastname: Vigorita
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D002460:Cell Line; D004247:DNA / Q000187:drug effects; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor; D018259:Herpesvirus 1, Human / Q000187:drug effects; D018258:Herpesvirus 2, Human / Q000187:drug effects; D006801:Humans; D007364:Intercalating Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D007372:Interferons / Q000096:biosynthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D010948:Viral Plaque Assay
chemical_list: D000970:Antineoplastic Agents; D000998:Antiviral Agents; D007364:Intercalating Agents; D009705:Nucleosides; D004247:DNA; D007372:Interferons