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Pyrido-Fused Deazapurine Bases: Synthesis and Glycosylation of 4-Substituted 9H-Pyrido[2′,3′:4,5]- and Pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidines

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    SYSNO ASEP0534197
    Document TypeJ - Journal Article
    R&D Document TypeJournal Article
    Subsidiary JČlánek ve WOS
    TitlePyrido-Fused Deazapurine Bases: Synthesis and Glycosylation of 4-Substituted 9H-Pyrido[2′,3′:4,5]- and Pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidines
    Author(s) Veselovská, Lucia (UOCHB-X) ORCID
    Pohl, Radek (UOCHB-X) RID, ORCID
    Tloušťová, Eva (UOCHB-X) RID, ORCID
    Gurská, S. (CZ)
    Džubák, P. (CZ)
    Hajdúch, M. (CZ)
    Hocek, Michal (UOCHB-X) RID, ORCID
    Source TitleACS Omega. - : American Chemical Society - ISSN 2470-1343
    Roč. 5, č. 40 (2020), s. 26278-26286
    Number of pages9 s.
    Languageeng - English
    CountryUS - United States
    KeywordsThymidylate synthase inhibitors ; receptor tyrosine kinase ; biological activity
    Subject RIVCC - Organic Chemistry
    OECD categoryOrganic chemistry
    R&D ProjectsGA19-08124S GA ČR - Czech Science Foundation (CSF)
    LM2015064 GA MŠMT - Ministry of Education, Youth and Sports (MEYS)
    Method of publishingOpen access
    Institutional supportUOCHB-X - RVO:61388963
    UT WOS000580943000083
    EID SCOPUS85094187095
    DOI10.1021/acsomega.0c04302
    AnnotationTwo isomeric sets of 4-substituted pyridopyrrolopyrimidine nucleobases were prepared through nucleophilic substitutions or cross-coupling reactions of 4-chloropyridopyrrolopyrimidines. The corresponding 4-amino-pyridopyrrolopyrimidines were glycosylated with 5-O-tritylribose using the modified Mitsunobu protocol. Several examples of the title heterocycles showed blue or green fluorescence. Testing of the pyridopyrrolopyrimidine nucleobases for the cytotoxic effect revealed micromolar activity of 4-benzofuryl derivatives in both series, preferentially in multidrug-resistant cancers.
    WorkplaceInstitute of Organic Chemistry and Biochemistry
    Contactasep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434
    Year of Publishing2021
    Electronic addresshttps://doi.org/10.1021/acsomega.0c04302
Number of the records: 1  

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