Collect. Czech. Chem. Commun. 2001, 66, 483-499
https://doi.org/10.1135/cccc20010483

Cytostatic 6-Arylpurine Nucleosides III. Synthesis and Structure-Activity Relationship Study in Cytostatic Activity of 6-Aryl-, 6-Hetaryl- and 6-Benzylpurine Ribonucleosides

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

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, CZ-166 10 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 fifteen 6-aryl-, 6-hetaryl- and 6-benzylpurine ribonucleosides has been prepared by Pd-catalyzed cross-coupling reactions of 6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)- purine with arylboronic acids, hetarylzinc halides, hetarylstannanes or benzylzinc halides followed by deprotection. Structure-activity relationship study revealed that besides 6-(4-substituted phenyl)purine nucleosides, also some 6-hetaryl- and 6-benzylpurine ribonucleosides possess considerable cytostatic activity.

Keywords: Purines; Nucleosides; Cross-coupling reactions; Antineoplastic agents; Antitumor activity; Arylboronic acids; Stannanes; Organozinc reagents; Suzuki reaction.

References: 22 live references.