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Synthesis of phosphonate derivatives of 2′-deoxy-2′-fluorotetradialdose D-nucleosides and tetradialdose D-nucleosides

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, ORCID}
Article 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	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 ; Viktorie Chládková, Tel.: 232 002 434
Year of Publishing	2022
Electronic address	https://doi.org/10.1016/j.tet.2021.132159

Number of the records: 1