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Synthesis of (purin-6-yl)acetates and their transformations to 6-(2-hydroxyethyl)- and 6-(carbamoylmethyl)purines
Zbyněk Hasník, Radek Pohl, Blanka Klepetářová and Michal Hocek
Language English Country Czech Republic
- MeSH
- Financing, Organized MeSH
- Nucleosides chemical synthesis MeSH
- Purines chemical synthesis MeSH
- Structure-Activity Relationship MeSH
A novel approach to the synthesis of (purin-6-yl)acetates was developed based on Pd-catalyzed cross-coupling reactions of 6-chloropurines with a Reformatsky reagent. Their reduction with NaBH4 and treatment with MnO2 gave 6-(2-hydroxyethyl)purines, while reactions with amines in presence of NaCN afforded 6-(carbamoylmethyl)purines. Mesylation of the 6-(2-hydroxyethyl)purines followed by nucleophilic substitutions gave rise to several 6-(2-substituted ethyl)purines. This methodology was successfully applied to the synthesis of substituted purine bases and nucleosides for cytostatic and antiviral activity screening. None of the compounds exerted significant activity.
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Lit.: 32
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- $a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic v.v.i., Gilead Sciences & IOCB Research Center, Flemingovo nám. 2, CZ-166 10 Prague 6, Czech Republic
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- $a Lit.: 32
- 520 9_
- $a A novel approach to the synthesis of (purin-6-yl)acetates was developed based on Pd-catalyzed cross-coupling reactions of 6-chloropurines with a Reformatsky reagent. Their reduction with NaBH4 and treatment with MnO2 gave 6-(2-hydroxyethyl)purines, while reactions with amines in presence of NaCN afforded 6-(carbamoylmethyl)purines. Mesylation of the 6-(2-hydroxyethyl)purines followed by nucleophilic substitutions gave rise to several 6-(2-substituted ethyl)purines. This methodology was successfully applied to the synthesis of substituted purine bases and nucleosides for cytostatic and antiviral activity screening. None of the compounds exerted significant activity.
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- $a nukleosidy $x chemická syntéza $7 D009705
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