Synthesis and biological activity of 4'-C-hydroxymethyl-2'-fluoro-D-arabinofuranosylpurine nucleosides.
A series of 4'-C-hydroxymethyl-2'-fluoro-D-arabinofuranosylpurine nucleosides was prepared and evaluated for cytotoxicity in human tumor cell lines. A convenient synthesis of the carbohydrate precursor 4-C-hydroxymethyl-3,5-di-O-benzoyl-2-fluoro-alpha-D-arabinofuranosyl bromide (13) was developed. Coupling of 13 with the sodium salt of 2,6-dichloropurine led to five target purine nucleosides.
Shortnacy-Fowler
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Southern Research Institute, P.O. Box 55305, Birmingham, Alabama 35255-5305, USA.
Tiwari
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Montgomery
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Secrist
J A
JA
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001087:Arabinonucleosides / Q000138:chemical synthesis* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology*; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000970:Antineoplastic Agents; D001087:Arabinonucleosides; D011684:Purine Nucleosides