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Synthesis of phosphonate derivatives of 2′-deoxy-2′-fluorotetradialdose D-nucleosides and tetradialdose D-nucleosides
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SYSNO ASEP 0543389 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis of phosphonate derivatives of 2′-deoxy-2′-fluorotetradialdose D-nucleosides and tetradialdose D-nucleosides Author(s) Lášek, Tomáš (UOCHB-X) ORCID
Dobiaš, Juraj (UOCHB-X) ORCID
Buděšínský, Miloš (UOCHB-X) RID, ORCID
Kozák, Jaroslav (UOCHB-X) RID, ORCID
Lapuníková, Barbora (UOCHB-X)
Rosenberg, Ivan (UOCHB-X) RID, ORCID
Birkuš, Gabriel (UOCHB-X) ORCID
Páv, Ondřej (UOCHB-X) RID, ORCIDArticle number 132159 Source Title Tetrahedron. - : Elsevier - ISSN 0040-4020
Roč. 89, Jun 4 (2021)Number of pages 18 s. Language eng - English Country GB - United Kingdom Keywords nucleoside phosphonate ; triphosphate ; prodrug ; tetradialdose d-nucleoside ; 2′-fluoronucleoside OECD category Organic chemistry R&D Projects EF16_019/0000729 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Limited access Institutional support UOCHB-X - RVO:61388963 UT WOS 000659206000014 EID SCOPUS 85104947933 DOI https://doi.org/10.1016/j.tet.2021.132159 Annotation Analogs of nucleosides and nucleotides represent a promising pool of potential therapeutics. This work describes a new synthetic route leading to 2′-deoxy-2′-fluorotetradialdose D-nucleoside phosphonates. Moreover, a new universal synthetic route leading to tetradialdose d-nucleosides bearing purine nucleobases is also described. All new compounds were tested as triphosphate analogs for inhibitory potency against a variety of viral polymerases. The fluorinated nucleosides were transformed to phosphoramidate prodrugs and evaluated in cell cultures against various viruses including influenza and SARS-CoV-2. 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 2022 Electronic address https://doi.org/10.1016/j.tet.2021.132159
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