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Synthesis and antiviral evaluation of a-l-2'-deoxythreofuranosyl nucleosides
journal contribution
posted on 2023-06-08, 19:00 authored by Kiran S Toti, Marco Derudas, Christopher McGuigan, Jan Balzarini, Serge Van CalenberghThe synthesis of a series of a-l-2'-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-a-l-threose, involving a Vorbrüggen coupling and a Barton-McCombie deoxygenation protocol as the key steps. All analogues, including a phosphoramidate nucleoside phosphate prodrug of the T analogue, were evaluated against a broad panel of different viruses but found inactive, while also lacking notable cellular toxicity. The thymidine analogue showed inhibition to mitochondrial thymidine kinase-2 (TK-2), herpes simplex virus type 1 (HSV-1) TK, varicella-zoster virus (VZV) TK and Mycobacterium tuberculosis thymidylate kinase.
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Publication status
- Published
Journal
European Journal of Medicinal ChemistryISSN
0223-5234Publisher
ElsevierExternal DOI
Issue
9Volume
46Page range
3704-3713Department affiliated with
- Chemistry Publications
Full text available
- No
Peer reviewed?
- Yes
Legacy Posted Date
2015-07-22Usage metrics
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