Issue 13, 2008
From the journal:

Organic & Biomolecular Chemistry

Synthesis of substituted 6-cyclopropylpurine bases and nucleosides by cross-coupling reactions or cyclopropanations†

Martin Kuchař,a   Radek Pohl,a   Blanka Klepetářová,a   Ivan Votrubaa  and  Michal Hocek*a  

* Corresponding authors

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead & IOCB Research Center, Flemingovo nam. 2, CZ-16610 Prague 6, Czech Republic
E-mail: hocek@uochb.cas.cz
Fax: +420 220183559
Tel: +420 220183324

Abstract

Synthesis of novel purine bases and nucleosides bearing unsubstituted or substituted cyclopropyl rings in position 6 is reported. Unsubstituted 6-cyclopropylpurines were efficiently prepared by cross-coupling reactions of 6-chloropurines with cyclopropylzinc chloride. 6-Vinylpurines underwent Cu-mediated cyclopropanations with ethyl diazoacetate to give 6-[(ethoxycarbonyl)cyclopropyl]purines that were further transformed to carboxylic acids, amides and alcohols. 6-Cyclopropylpurine ribonucleoside exerted a significant cytostatic effect while all substituted derivatives were inactive.

Graphical abstract: Synthesis of substituted 6-cyclopropylpurine bases and nucleosides by cross-coupling reactions or cyclopropanations

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Article information

DOI
https://doi.org/10.1039/B802833H
Article type
Paper
Submitted
19 Feb 2008
Accepted
11 Apr 2008
First published
02 May 2008

Org. Biomol. Chem., 2008,6, 2377-2387

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Synthesis of substituted 6-cyclopropylpurine bases and nucleosides by cross-coupling reactions or cyclopropanations

M. Kuchař, R. Pohl, B. Klepetářová, I. Votruba and M. Hocek, Org. Biomol. Chem., 2008, 6, 2377 DOI: 10.1039/B802833H

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