0543389 - ÚOCHB 2022 RIV GB eng J - Journal Article
Lášek, Tomáš - Dobiaš, Juraj - Buděšínský, Miloš - Kozák, Jaroslav - Lapuníková, Barbora - Rosenberg, Ivan - Birkuš, Gabriel - Páv, Ondřej
Synthesis of phosphonate derivatives of 2′-deoxy-2′-fluorotetradialdose D-nucleosides and tetradialdose D-nucleosides.
Tetrahedron. Roč. 89, Jun 4 (2021), č. článku 132159. ISSN 0040-4020. E-ISSN 1464-5416
R&D Projects: GA MŠMT(CZ) EF16_019/0000729
Institutional support: RVO:61388963
Keywords : nucleoside phosphonate * triphosphate * prodrug * tetradialdose d-nucleoside * 2′-fluoronucleoside
OECD category: Organic chemistry
Impact factor: 2.388, year: 2021 ; AIS: 0.377, rok: 2021
Method of publishing: Limited access
Result website:
https://doi.org/10.1016/j.tet.2021.132159DOI: https://doi.org/10.1016/j.tet.2021.132159

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.
Permanent Link: http://hdl.handle.net/11104/0320603