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

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Title:Cytostatic 6-Arylpurine Nucleosides V. Synthesis of 8-Substituted 6-Phenylpurine Ribonucleosides
Creators:
Hocek, Michal
Hocková, Dana
Štambaský, Jan
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 68, 5, pp. 837-848
Uncontrolled Keywords:Purines, Antineoplastic agents, Nucleosides, Halodeaminations, Suzuki-Miyaura reaction, Cross-coupling reactions, Nucleophilic substitutions

Abstract

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

Title:Cytostatic 6-Arylpurine Nucleosides V. Synthesis of 8-Substituted 6-Phenylpurine Ribonucleosides
Creators:
Hocek, Michal
Hocková, Dana
Štambaský, Jan
Uncontrolled Keywords:Purines, Antineoplastic agents, Nucleosides, Halodeaminations, Suzuki-Miyaura reaction, Cross-coupling reactions, Nucleophilic substitutions
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:68
Number:5
Page Range:pp. 837-848
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20030837UNSPECIFIED
ID Code:2088
Item Type:Article
Deposited On:06 Feb 2009 17:15
Last Modified:06 Feb 2009 16:15

Citation

Hocek, Michal; Hocková, Dana; Štambaský, Jan (2003) Cytostatic 6-Arylpurine Nucleosides V. Synthesis of 8-Substituted 6-Phenylpurine Ribonucleosides. Collection of Czechoslovak Chemical Communications, 68 (5). pp. 837-848. ISSN 0010-0765

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