Collect. Czech. Chem. Commun. 2003, 68, 837-848

Cytostatic 6-Arylpurine Nucleosides V. Synthesis of 8-Substituted 6-Phenylpurine Ribonucleosides

Michal Hocek*, Dana Hocková and Jan Štambaský

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, CZ-16610 Prague 6, Czech Republic


Regioselective Suzuki-Miyaura reaction of 8-bromo-6-iodo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine with phenylboronic acid gave 8-bromo-6-phenylpurine derivative that was used for cross-coupling reactions (with PhB(OH)2, Me3Al, Et3Al, BnZnCl) or nucleophilic substitutions (with NaOH, NaOMe, NH3, NHMe2 or thiourea). A series of 8-X-substituted 6-phenyl-9-(β-D-ribofuranosyl)purines (X = Ph, Me, Et, Bn, OH, OMe, NH2, NMe2, SH) was prepared in this way directly or after deprotection. None of the title nucleosides exhibited any considerable cytostatic activity.

Keywords: Purines; Nucleosides; Cross-coupling reactions; Nucleophilic substitutions; Suzuki-Miyaura reaction; Halodeaminations; Antineoplastic agents.

References: 29 live references.