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Synthesis, Photophysical Properties, and Biological Profiling of Benzothieno-Fused 7-Deazapurine Ribonucleosides
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SYSNO ASEP 0531532 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis, Photophysical Properties, and Biological Profiling of Benzothieno-Fused 7-Deazapurine Ribonucleosides Author(s) Yang, Chao (UOCHB-X) ORCID
Pohl, Radek (UOCHB-X) RID, ORCID
Tichý, Michal (UOCHB-X) RID, ORCID
Gurská, S. (CZ)
Pavliš, P. (CZ)
Džubák, P. (CZ)
Hajdúch, M. (CZ)
Hocek, Michal (UOCHB-X) RID, ORCIDSource Title Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
Roč. 85, č. 12 (2020), s. 8085-8101Number of pages 17 s. Language eng - English Country US - United States Keywords nucleoside ; inhibitors ; antitumor Subject RIV CC - Organic Chemistry OECD category Organic chemistry R&D Projects GA19-08124S GA ČR - Czech Science Foundation (CSF) NV15-31984A GA MZd - Ministry of Health (MZ) LM2015064 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Limited access Institutional support UOCHB-X - RVO:61388963 UT WOS 000543667400042 EID SCOPUS 85087814803 DOI 10.1021/acs.joc.0c00927 Annotation 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 Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2021 Electronic address https://doi.org/10.1021/acs.joc.0c00927
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