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ACS Comb Sci. 2015 Jul 13;17(7):426-32. doi: 10.1021/acscombsci.5b00071. Epub 2015 Jun 25.

Synthesis of Novel N9-Substituted Purine Derivatives from Polymer Supported α-Amino Acids.

Author information

1
†Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacký University, 771 46 Olomouc, Czech Republic.

Abstract

Solid-phase synthesis of purine derivatives bearing an α-amino acid motif in position 9 is described herein. Polymer supported amines were acylated with various Fmoc-α-amino acids and, after cleavage of the protecting group, arylation with 4,6-dichloro-5-nitropyrimidine or 2,4-dichloro-5-nitropyrimidine was performed. The second chlorine atom was replaced with various amines. Subsequent reduction of the nitro group, followed by reaction with aldehydes, afforded the purine scaffold. After cleavage from the polymer support, the target compounds were obtained in very good crude purity, good overall yields, and excellent enantiomeric purity. The anticancer activity of prepared compounds was tested in vitro against human cancer cell lines MCF7 and K562, and they were found to have mild, but clear dose-dependent effects.

KEYWORDS:

anticancer activity; purine derivatives; solid-phase synthesis; α-amino acids

PMID:
26098936
DOI:
10.1021/acscombsci.5b00071
[Indexed for MEDLINE]

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