Synthesis and Antiviral Activity of 2′-Modified L-Nucleoside Analogues

0582961 - BC 2024 RIV US eng J - Journal Article
Penjarla, S. - Reddy, P.Y. - Penta, S. - Sanghvi, Y.S. - Eyer, Luděk - Štefánik, M. - Krátká, Z. - Růžek, Daniel - Banerjee, S.
Synthesis and Antiviral Activity of 2′-Modified L-Nucleoside Analogues.
ChemistrySelect. Roč. 8, č. 48 (2023), č. článku e202303585. ISSN 2365-6549. E-ISSN 2365-6549
R&D Projects: GA MŠMT(CZ) LTAUSA18016
Institutional support: RVO:60077344
Keywords : scale synthesis * pyrimidine * uridine * Antiviral Agent * L-2, 2'-anhydrouridine * L-Arabinose * Cytotoxicity * L-Nucleoside
OECD category: Microbiology
Impact factor: 2.1, year: 2022
Method of publishing: Limited access
https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/slct.202303585

Nucleoside analogues have been the foundation of antiviral therapy over the past few decades. D-nucleosides with natural stereochemistry occupies the lion share of the marketed antiviral agents. However, much less effort have been put towards the development of L-nucleosides as antiviral agents. Herein, our effort towards the synthesis of 2 'substituted L-nucleoside analogues is reported as an emerging class of antiviral agents. Biological activity of the synthesized L-nucleosided was evaluated against two viruses of importance, tick-borne encephalitis virus (TBEV) and Severe Acute Respiratory Syndrome Coronavirus-2 (SARS-CoV-2) in adenocarcinomic human alveolar basal epithelial cells (A459) and Vero cells. Ring opening of L-2, 2 '-Anhydrouridine (2) with various nucleophiles to make several 2'-substituted L-nucleosides is the key synthetic outcome. This development has paved the way in the synthesis of many new analogues of 2'-substituted L-nucleosides for numerous applications.
Permanent Link: https://hdl.handle.net/11104/0351001