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ID: ALA1821600
Journal: Eur J Med Chem
Title: Synthesis and antiviral evaluation of α-L-2'-deoxythreofuranosyl nucleosides.
Authors: Toti KS, Derudas M, McGuigan C, Balzarini J, Van Calenbergh S.
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.
CiteXplore: 21664010