Collect. Czech. Chem. Commun. 2000, 65, 1683-1697
https://doi.org/10.1135/cccc20001683

Cytostatic 6-Arylpurine Nucleosides II. Synthesis of Sugar-Modified Derivatives: 9-(2-Deoxy-β-D-erythro-pentofuranosyl)-, 9-(5-Deoxy-β-D-ribofuranosyl)- and 9-(2,3-Dihydroxypropyl)-6-phenylpurines

Michal Hoceka,*, Antonín Holýa, Ivan Votrubaa and Hana Dvořákováb

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, CZ-16610 Prague 6, Czech Republic
b Laboratory of NMR Spectroscopy, Institute of Chemical Technology, Prague, CZ-166 28 Prague 6, Czech Republic

This article is part of serial Cytostatic 6-Arylpurine Nucleosides.

Abstract

9-(2-Deoxy-β-D-erythro-pentofuranosyl)-6-(4-substituted phenyl)purines, 9-(5-deoxy-β-D-ribofuranosyl)-6-(4-substituted phenyl)purines and 9-(2,3-dihydroxypropyl)-6-(4-substituted phenyl)purines were prepared by the Suzuki-Miyaura cross-coupling reactions of the corresponding protected 9-substituted 6-chloropurines with substituted phenylboronic acids followed by MeONa mediated deprotection. In contrast to the highly active 6-phenylpurine ribonucleosides, the title compounds did not show any considerable cytostatic activity.

Keywords: Purines; Nucleosides; Cross-coupling reactions; Boronic acids; Acyclic nucleoside analogues; 5'-Deoxyribonucleosides; 2'-Deoxyribonucleosides; Cytostatic activity; Antitumor agents.

References: 23 live references.