title: Synthesis of 2'-deoxy-2'-fluoro-4'-thioarabinonucleosides using the Pummerer rearrangement and their biological evaluation.
abstract: Searching for more effective antineoplastic and antiviral agents, we have prepared various 2'-deoxy-2'-fluoro-4'-thioarabinonucleosides. The glycosylation reaction of persilylated pyrimidine bases with a 4-thiosugar derivative was performed using SnCl4 as a catalyst. The same reaction between purines and the 4-thiosugar, catalyzed by TMSOTf, gave the corresponding purine 4'-thionucleosides. Pyrimidine derivatives (e.g., 5-ethyluracil, 5-iodouracil, and 5-iodocytosine) showed potent anti-HSV-1 activities, and guanine and 2,6-diaminopurine derivatives showed marked anti-HCMV activities.
authors.affiliation: Biochemicals Division, Yamasa Corporation, Chiba, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Yoshimura
authors.forename: K
authors.initials: K
authors.lastname: Kitano
authors.forename: K
authors.initials: K
authors.lastname: Yamada
authors.forename: S
authors.initials: S
authors.lastname: Sakata
authors.forename: S
authors.initials: S
authors.lastname: Miura
authors.forename: N
authors.initials: N
authors.lastname: Ashida
authors.forename: H
authors.initials: H
authors.lastname: Machida
authors.forename: A
authors.initials: A
authors.lastname: Matsuda
mesh_terms: D000964:Antimetabolites, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D002384:Catalysis; D018259:Herpesvirus 1, Human / Q000187:drug effects; D006801:Humans; D007202:Indicators and Reagents; D007624:KB Cells; D015458:Leukemia, T-Cell; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013872:Thionucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D014407:Tumor Cells, Cultured
chemical_list: D000964:Antimetabolites, Antineoplastic; D000998:Antiviral Agents; D007202:Indicators and Reagents; D013872:Thionucleosides