Synthesis of 2-Substituted 6-(Hydroxymethyl)purine Bases and Nucleosides

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Title:Synthesis of 2-Substituted 6-(Hydroxymethyl)purine Bases and Nucleosides
Creators:
Šilhár, Peter
Pohl, Radek
Votruba, Ivan
Hocek, Michal
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 70, 10, pp. 1669-1695
Uncontrolled Keywords:Hydroxymethylation, Palladium, Purines, Nucleosides, Cytostatic activity, Functionalized organozinc reagents, Cross-coupling reactions, Adenosine deaminase

Abstract

A facile and efficient methodology of the synthesis of 6-(hydroxymethyl)purine derivatives (bases and nucleosides) was developed based on Pd-catalyzed cross-coupling reactions of 6-halopurines or <i>N</i>-protected 2-amino-6-halopurines with (benzoyloxymethyl)zinc iodide followed by deprotection. Regioselective hydroxymethylations of 2,6-dihalopurines were also studied and used for the synthesis of 2-chloro-6-(hydroxymethyl)- or 2,6-bis(hydroxymethyl)purines. The 6-(hydroxymethyl)purine ribonucleoside <strong>5f</strong> exerted high cytostatic effect and moderate inhibition of adenosine deaminase, while all the other derivatives were much less effective or entirely inactive. <p>

Title:Synthesis of 2-Substituted 6-(Hydroxymethyl)purine Bases and Nucleosides
Creators:
Šilhár, Peter
Pohl, Radek
Votruba, Ivan
Hocek, Michal
Uncontrolled Keywords:Hydroxymethylation, Palladium, Purines, Nucleosides, Cytostatic activity, Functionalized organozinc reagents, Cross-coupling reactions, Adenosine deaminase
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:70
Number:10
Page Range:pp. 1669-1695
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20051669UNSPECIFIED
ID Code:2432
Item Type:Article
Deposited On:06 Feb 2009 17:18
Last Modified:06 Feb 2009 16:18

Citation

Šilhár, Peter; Pohl, Radek; Votruba, Ivan; Hocek, Michal (2005) Synthesis of 2-Substituted 6-(Hydroxymethyl)purine Bases and Nucleosides. Collection of Czechoslovak Chemical Communications, 70 (10). pp. 1669-1695. ISSN 0010-0765

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