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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 Calenbergh
The 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.

History

Publication status

  • Published

Journal

European Journal of Medicinal Chemistry

ISSN

0223-5234

Publisher

Elsevier

Issue

9

Volume

46

Page range

3704-3713

Department affiliated with

  • Chemistry Publications

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2015-07-22

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