title: Synthesis and biological evaluation of L- and D-configuration 1,3-dioxolane 5-azacytosine and 6-azathymine nucleosides.
abstract: Novel L- and D-configuration dioxolane 5-azacytosine and 6-azathymine nucleosides have been synthesized and evaluated for biological activity. (-)-(2S,4S)-1-[2-(Hydroxymethyl)-1,3-dioxolan-4-yl]-5-azacytosine (6) showed significant activity against HBV, whereas the D-configuration analogue (14) has been found to exhibit potent anti-HIV activity.
authors.affiliation: Department of Pharmacology and Developmental Therapeutics Program, Cancer Center, Yale University School of Medicine, New Haven, CT 06520-8066, USA.
authors.forename: M Z
authors.initials: MZ
authors.lastname: Luo
authors.forename: M C
authors.initials: MC
authors.lastname: Liu
authors.forename: D E
authors.initials: DE
authors.lastname: Mozdziesz
authors.forename: T S
authors.initials: TS
authors.lastname: Lin
authors.forename: G E
authors.initials: GE
authors.lastname: Dutschman
authors.forename: E A
authors.initials: EA
authors.lastname: Gullen
authors.forename: Y C
authors.initials: YC
authors.lastname: Cheng
authors.forename: A C
authors.initials: AC
authors.lastname: Sartorelli
mesh_terms: D000818:Animals; D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D003596:Cytosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004148:Dioxolanes / Q000138:chemical synthesis / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects; D006515:Hepatitis B virus / Q000187:drug effects; D018259:Herpesvirus 1, Human / Q000187:drug effects; D018258:Herpesvirus 2, Human / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013941:Thymine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D014407:Tumor Cells, Cultured / Q000187:drug effects
chemical_list: D019380:Anti-HIV Agents; D000970:Antineoplastic Agents; D000998:Antiviral Agents; D004148:Dioxolanes; D009705:Nucleosides; C039854:5-azacytosine; D003596:Cytosine; D013941:Thymine; C010962:formal glycol; C039857:6-azathymine