Collect. Czech. Chem. Commun. 2006, 71, 1484-1496
https://doi.org/10.1135/cccc20061484

Cytostatic and Antiviral 6-Arylpurine Ribonucleosides VIII. Synthesis and Evaluation of 6-Substituted Purine 3'-Deoxyribonucleosides

Michal Hocek*, Peter Šilhár and Radek Pohl

Gilead Sciences & IOCB Research Center, Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, CZ-16610 Prague 6, Czech Republic

This article is part of serial Cytostatic and Antiviral 6-Arylpurine Ribonucleosides.

Abstract

A series of purine 3'-deoxyribonucleosides bearing diverse C-substituents (alkyl, aryl, hetaryl or hydroxymethyl) in the position 6 was prepared by Pd-catalyzed cross-coupling reactions of 6-iodo-9-[2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-β-D-ribofuranosyl]purine with the corresponding organometallics followed by deprotection by (HF)3·Et3N. None of the title 3'-deoxyribonucleoside showed any cytostatic activity or anti-HCV effect in replicon assay.

Keywords: Purines; Nucleosides; Cross-coupling reactions; Antivirals; HCV; Cordycepin.

References: 41 live references.