Synthesis and biological profiling of 6-or 7-(het)aryl-7-deazapurine 4 '-C-methylribonucleosides
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F15%3A10314362" target="_blank" >RIV/00216208:11310/15:10314362 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/15:00454134 RIV/61989592:15110/15:33156400
Result on the web
<a href="http://dx.doi.org/10.1016/j.bmc.2015.10.040" target="_blank" >http://dx.doi.org/10.1016/j.bmc.2015.10.040</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.bmc.2015.10.040" target="_blank" >10.1016/j.bmc.2015.10.040</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis and biological profiling of 6-or 7-(het)aryl-7-deazapurine 4 '-C-methylribonucleosides
Original language description
The synthesis and biological activity profiling of a large series of diverse pyrrolo[2,3-d]pyrimidine 4 '-C-methylribonucleosides bearing an (het) aryl group at position 4 or 5 is reported as well as the synthesis of several phosphoramidate prodrugs. These compounds are 4 '-C-methyl derivatives of previously reported cytostatic hetaryl-7-deazapurine ribonucleosides. The synthesis is based on glycosylation of halogenated 7-deazapurine bases with 1,2-di-O-acetyl-3,5-di-O-benzyl-4-C-methyl-beta-D-ribofuranose followed by cross-coupling and nucleophilic substitution reactions. The final compounds showed low cytotoxicity and several derivatives exerted antiviral activity against HCV or Dengue viruses at micromolar concentrations.
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
<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
S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2015
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Bioorganic and Medicinal Chemistry
ISSN
0968-0896
e-ISSN
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Volume of the periodical
23
Issue of the periodical within the volume
23
Country of publishing house
GB - UNITED KINGDOM
Number of pages
17
Pages from-to
7422-7438
UT code for WoS article
000364847200009
EID of the result in the Scopus database
2-s2.0-84947550562