Title: Norbornane-based nucleoside and nucleotide analogues locked in North conformation
Authors: Dejmek, Milan ×
Šála, Michal
Hřebabecký, Hubert
Dračínský, Martin
Procházková, Eliška
Chalupská, Dominika
Klíma, Martin
Plačková, Pavla
Hájek, Miroslav
Andrei, Graciela
Naesens, Lieve
Leyssen, Pieter
Neyts, Johan
Balzarini, Jan
Boura, Evzen
Nencka, Radim #
Issue Date: Jan-2015
Publisher: Pergamon
Series Title: Bioorganic & Medicinal Chemistry vol:23 issue:1 pages:184-191
Article number: S0968-0896(14)00798-6
Abstract: We report on the synthesis of novel conformationally locked nucleoside and nucleotide derivatives, which are structurally closely related to clinically used antivirals such as didanosine and abacavir. As a suitable conformationally rigid substitute of the sugar/pseudosugar ring allowing a permanent stabilization of the nucleoside in North conformation we employed bicyclo[2.2.1]heptane (norbornane) substituted in the bridgehead position with a hydroxymethyl group and in the C-3 position with a nucleobase. Prepared nucleoside derivatives were also converted into appropriate phosphoramidate prodrugs (ProTides) in order to increase delivery of the compounds in the cells. All target compounds were evaluated in a broad antiviral and cytostatic assay panel.
ISSN: 0968-0896
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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