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Synthesis and antiviral evaluation of α-l-2'-deoxythreofuranosyl nucleosides.

Toti, K. S., Derudas, Marco, McGuigan, Christopher, Balzarini, J and Van Calenbergh, S 2011. Synthesis and antiviral evaluation of α-l-2'-deoxythreofuranosyl nucleosides. European Journal of Medicinal Chemistry

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Abstract

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
Date Type: Publication
Status: Published
Schools: Pharmacy
Systems Immunity Research Institute (SIURI)
Subjects: R Medicine > RS Pharmacy and materia medica
ISSN: 0223-5234
Last Modified: 18 Oct 2017 13:27
URI: http://orca.cf.ac.uk/id/eprint/6992

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