Design and synthesis of DNA-intercalating 9-fluoren-beta-O-glycosides as potential IFN-inducers, and antiviral and cytostatic agents.
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.
Alcaro
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S
Dipartimento di Scienze Farmacobiologiche, Università di Catanzaro 'Magna Graecia', Complesso Ninì Barbieri - 88021 Roccelletta di Borgia (CZ), Italy.
Arena
A
A
Neri
S
S
Ottanà
R
R
Ortuso
F
F
Pavone
B
B
Vigorita
M G
MG
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
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D007364:Intercalating Agents; D009705:Nucleosides; D004247:DNA; D007372:Interferons