Collect. Czech. Chem. Commun. 2002, 67, 325-335
https://doi.org/10.1135/cccc20020325

Cytostatic 6-Arylpurine Nucleosides IV. Synthesis of 2-Substituted 6-Phenylpurine Ribonucleosides

Michal Hoceka,*, Antonín Holýa 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

A series of 2-X-substituted-6-phenyl-9-(β-D-ribofuranosyl)purines (X = Cl, Br, I, CH3, CF3 and Ph) was prepared by halo-deaminations of protected 2-amino-6-phenylpurine ribonucleoside, by regioselective Suzuki-Miyaura reactions of 2,6-dihalopurines with phenylboronic acid or by cross-coupling reactions of the corresponding 2-halo-6-phenylpurines followed by deprotection. None of the title nucleosides exhibited any considerable cytostatic activity.

Keywords: Purines; Nucleosides; Cross-coupling reactions; Antineoplastic agents; Deaminations; Trifluoromethylation.

References: 23 live references.