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Synthesis and Cytotoxic and Antiviral Activity Profiling of All-Four Isomeric Series of Pyrido-Fused 7-Deazapurine Ribonucleosides
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SYSNO ASEP 0532766 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis and Cytotoxic and Antiviral Activity Profiling of All-Four Isomeric Series of Pyrido-Fused 7-Deazapurine Ribonucleosides Author(s) Veselovská, Lucia (UOCHB-X) ORCID
Kudlová, N. (CZ)
Gurská, S. (CZ)
Lišková, B. (CZ)
Medvedíková, M. (CZ)
Hodek, Ondřej (UOCHB-X) ORCID, RID
Tloušťová, Eva (UOCHB-X) RID, ORCID
Milisavljevič, Nemanja (UOCHB-X)
Tichý, Michal (UOCHB-X) RID, ORCID
Perlíková, Pavla (UOCHB-X) RID, ORCID
Mertlíková-Kaiserová, Helena (UOCHB-X) RID, ORCID
Trylčová, Jana (UOCHB-X) ORCID
Pohl, Radek (UOCHB-X) RID, ORCID
Klepetářová, Blanka (UOCHB-X) RID, ORCID
Džubák, P. (CZ)
Hajdúch, M. (CZ)
Hocek, Michal (UOCHB-X) RID, ORCIDSource Title Chemistry - A European Journal. - : Wiley - ISSN 0947-6539
Roč. 26, č. 57 (2020), s. 13002-13015Number of pages 14 s. Language eng - English Country DE - Germany Keywords antitumor agents ; antiviral agents ; drug discovery ; phosphorylation ; ribonucleosides 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 000569396400001 EID SCOPUS 85087796936 DOI 10.1002/chem.202001124 Annotation All four isomeric series of novel 4‐substituted pyrido‐fused 7‐deazapurine ribonucleosides possessing the pyridine nitrogen atom at different positions were designed and synthesized. The total synthesis of each isomeric fused heterocycle through multistep heterocyclization was followed by glycosylation and derivatization at position 4 by cross‐coupling reactions or nucleophilic substitutions. All compounds were tested for cytostatic and antiviral activity. The most active were pyrido[4′,3′:4,5]pyrimidine nucleosides bearing MeO, NH2, MeS, or CH3 groups at position 4, which showed submicromolar cytotoxic effects and good selectivity for cancer cells. The mechanism involved activation by phosphorylation and incorporation to DNA where the presence of the modified ribonucleosides causes double‐strand breaks and apoptosis. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Year of Publishing 2021 Electronic address https://doi.org/10.1002/chem.202001124
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