Sugar-modified derivatives of cytostatic 6-(het)aryl-7-deazapurine nucleosides: 2'-C-methylribonucleosides, arabinonucleosides and 2'-deoxy-2'-fluoroarabinonucleosides
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F11%3A00361463" target="_blank" >RIV/61388963:_____/11:00361463 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1135/cccc2011082" target="_blank" >http://dx.doi.org/10.1135/cccc2011082</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1135/cccc2011082" target="_blank" >10.1135/cccc2011082</a>
Alternative languages
Result language
angličtina
Original language name
Sugar-modified derivatives of cytostatic 6-(het)aryl-7-deazapurine nucleosides: 2'-C-methylribonucleosides, arabinonucleosides and 2'-deoxy-2'-fluoroarabinonucleosides
Original language description
A series of novel sugar-modified derivatives of cytostatic 6-hetaryl-7-deazapurine ribonucleosides: 2'-C-methylribonucleosides, arabinonucleosides and 2'-deoxy-2'-fluoroarabinonucleosides bearing an alkyl, aryl and hetaryl group in position 6 were prepared by palladium catalyzed cross-coupling reactions of corresponding 6-chloro-(7-fluoro)-7-deazapurine nucleosides with (het)arylboronic, hetarylstannanes and trimethylaluminium. Key intermediate 6-chloro-7-deazapurine 2'-C-methyl-beta-D-ribofuranoside was prepared via a stereoselective nucleobase anion glycosylation with toluoyl protected 1,2-anhydro-2-C-methylribofuranose. The 6-chloro-7-deazapurine arabinofuranoside intermediate was obtained by epimerization from 3',5'-protected 6-chloro-7-deazapurineribofuranoside via 2-hydroxyl oxidation followed by reduction. None of the prepared compounds showed any considerable cytostatic or antiviral activity.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
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Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)
Others
Publication year
2011
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Collection of Czechoslovak Chemical Communications
ISSN
0010-0765
e-ISSN
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Volume of the periodical
76
Issue of the periodical within the volume
8
Country of publishing house
CZ - CZECH REPUBLIC
Number of pages
31
Pages from-to
957-988
UT code for WoS article
000298002900003
EID of the result in the Scopus database
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