title: Does the anti-hepatitis B virus activity of (+)-5'-noraristeromycin exist in its 4'-epimer and 4'-deoxygenated derivatives?
abstract: To begin an exploration of the structural parameters responsible for the activity of (+)-5'-noraristeromycin toward hepatitis B virus (HBV), three derivatives varied at the C-4' position have been prepared and evaluated. The syntheses began with a Mitsunobu coupling reaction of an appropriate cyclopentanol with 6-chloropurine. The products of these reactions were synthetically altered by standard ammonolysis and deprotection procedures to give the desired products. Evaluation of the new derivatives indicated that removal of the C-4' hydroxyl of (+)-5'-noraristeromycin increased its potency toward HBV by approximately 10-fold.
authors.affiliation: Georgetown University Medical Center, Division of Molecular Virology and Immunology, Rockville, Maryland 20852, USA.
authors.forename: K L
authors.initials: KL
authors.lastname: Seley
authors.forename: S W
authors.initials: SW
authors.lastname: Schneller
authors.forename: B
authors.initials: B
authors.lastname: Korba
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006515:Hepatitis B virus / Q000187:drug effects* / Q000502:physiology; D006801:Humans; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured; D014779:Virus Replication / Q000187:drug effects
chemical_list: D000998:Antiviral Agents; C076829:5'-noraristeromycin; D000241:Adenosine