Synthesis and antiviral evaluation of α-l-2′-deoxythreofuranosyl nucleosides

Toti, Kiran S, Derudas, Marco, McGuigan, Christopher, Balzarini, Jan and Van Calenbergh, Serge (2011) Synthesis and antiviral evaluation of α-l-2′-deoxythreofuranosyl nucleosides. European Journal of Medicinal Chemistry, 46 (9). pp. 3704-3713. ISSN 0223-5234

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The synthesis of a series of α-l-2′-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-α-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.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: Marco Derudas
Date Deposited: 22 Jul 2015 15:13
Last Modified: 22 Jul 2015 15:13
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