Title: Synthesis and antiviral evaluation of α-l-2'-deoxythreofuranosyl nucleosides
Authors: Toti, Kiran S ×
Derudas, Marco
McGuigan, Christopher
Balzarini, Jan
Van Calenbergh, Serge #
Issue Date: Sep-2011
Series Title: European Journal of Medicinal Chemistry vol:46 issue:9 pages:3704-13
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.
ISSN: 0223-5234
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
× corresponding author
# (joint) last author

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