Synthesis and Cytostatic and Antiviral Activities of 2 '-Deoxy-2 ',2 '-difluororibo- and 2 '-Deoxy-2 '-fluororibonucleosides Derived from 7-(Het)aryl-7-deazaadenines

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F13%3A10159265" target="_blank" >RIV/00216208:11310/13:10159265 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/13:00393973
Result on the web
<a href="http://dx.doi.org/10.1002/cmdc.201300047" target="_blank" >http://dx.doi.org/10.1002/cmdc.201300047</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/cmdc.201300047" target="_blank" >10.1002/cmdc.201300047</a>

Result language
angličtina
Original language name
Synthesis and Cytostatic and Antiviral Activities of 2 '-Deoxy-2 ',2 '-difluororibo- and 2 '-Deoxy-2 '-fluororibonucleosides Derived from 7-(Het)aryl-7-deazaadenines
Original language description
A series of sugar-modified derivatives of cytostatic 7-heteroaryl-7-deazaadenosines (2-deoxy-2-fluororibo- and 2-deoxy-2,2-difluororibonucleosides) bearing an aryl or heteroaryl group at position7 was prepared and screened for biological activity. The difluororibonucleosides were prepared by non- stereoselective glycosidation of 6-chloro-7-deazapurine with benzoyl-protected 2-deoxy-2,2-difluoro-D-erythro-pentofuranosyl-1-mesylate, followed by amination and aqueous Suzuki cross-couplings with (het)arylboronic acids. The fluororibo derivatives were prepared by aqueous palladium-catalyzed cross-coupling reactions of the corresponding 7-iodo-7-deazaadenine 2-deoxy-2-fluororibonucleoside 20 with (het)arylboronic acids. The key intermediate 20 was prepared by a six-step sequence from the corresponding arabinonucleoside by selective protection of 3- and 5-hydroxy groups with acid-labile groups, followed by stereoselective SN2 fluorination and deprotection. Some of the title nucleosides and 7-
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
—

Project
<a href="/en/project/GAP207%2F11%2F0344" target="_blank" >GAP207/11/0344: Combinatorial and rational approaches for the synthesis and evaluation of novel modified nucleosides with cytostatic and antimicrobial activity</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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