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  • Title: Cytostatic and antiviral 6-arylpurine ribonucleosides. Part 7: synthesis and evaluation of 6-substituted purine l-ribonucleosides.
    Author: Hocek M, Silhár P, Shih IH, Mabery E, Mackman R.
    Journal: Bioorg Med Chem Lett; 2006 Oct 15; 16(20):5290-3. PubMed ID: 16905315.
    Abstract:
    A series of purine l-ribonucleosides 2a-2i bearing diverse C-substituents (alkyl, aryl, hetaryl or hydroxymethyl) in the position 6 were prepared by Pd-catalyzed cross-coupling reactions of 6-chloro-9-(2,3,5-tri-O-acetyl-beta-l-ribofuranosyl)purine with the corresponding organometallics followed by deprotection. Unlike their d-ribonucleoside enantiomers that possess strong cytostatic and anti-HCV activity, the l-ribonucleosides were inactive except for 6-benzylpurine nucleoside 2h showing moderate anti-HCV effect in replicon assay. A triphosphate of 2h did not inhibit HCV RNA polymerase.
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