Synthesis, Photophysical Properties, and Biological Profiling of Benzothieno-Fused 7-Deazapurine Ribonucleosides

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F20%3A00531532" target="_blank" >RIV/61388963:_____/20:00531532 - isvavai.cz</a>
Alternative codes found
RIV/61989592:15110/20:73601334 RIV/00216208:11310/20:10414605
Result on the web
<a href="https://doi.org/10.1021/acs.joc.0c00927" target="_blank" >https://doi.org/10.1021/acs.joc.0c00927</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.0c00927" target="_blank" >10.1021/acs.joc.0c00927</a>

Result language
angličtina
Original language name
Synthesis, Photophysical Properties, and Biological Profiling of Benzothieno-Fused 7-Deazapurine Ribonucleosides
Original language description
Two isomeric series of benzothieno-fused 7-deazapurine (benzo[4′,5′]thieno[3′,2′:4,5]- and benzo[4′,5′]thieno[2′,3′:4,5]pyrrolo[2,3-d]pyrimidine) ribonucleosides were designed and synthesized. Key steps of the synthesis included the Negishi coupling of zincated dichloropyrimidine with 2- or 3-iodobenzothiophene followed by azidation, thermal or photochemical cyclization, glycosylation, and final functionalization at position 6 through cross-couplings or nucleophilic substitutions. Deprotection gave the final nucleosides, some of which showed moderate cytotoxic and antiviral activity. Most of the free nucleosides showed moderate to strong fluorescence with emission maxima of 362–554 nm. 2′-Deoxyribonucleoside and its 5′-O-triphosphate were also prepared from benzothieno-fused 7-deazaadenine derivative, and the triphosphate was a good substrate for KOD XL DNA polymerase in primer extension synthesis of modified DNA which exerted a weak fluorescence which was slightly enhanced in double-stranded DNA as compared to single-stranded oligonucleotides
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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