Title: Design, synthesis, and biological evaluation of Cl-phosphonamidate analogues of 2-deoxy-D-ribose-l-phosphate
Authors: Quintiliani, Maurizio ×
Balzarini, Jan
McGuigan, Christopher #
Issue Date: Nov-2013
Publisher: Pergamon Press
Series Title: Tetrahedron vol:69 issue:43 pages:9111-9119
Abstract: A novel series of phenoxy C1-phosphonamidate derivatives of 2-deoxy-D-ribose have been synthesised as stable analogues of 2-deoxy-alpha-n-ribose-1-phosphate. A number of synthetic routes were explored for the preparation of these targets. The successful approach involved the synthesis of a protected C1-phosphonate ester 17 via Michaelis Arbuzov reaction, which was then hydrolysed and coupled with different amino acid esters using aldrithiol. Subsequent hydrogenolysis afforded the targets 2a-g, which were isolated as a mixture of diastereoisomers. The compounds were assayed for inhibition of thymidine phosphorylase (TP) and uridine phosphorylase (UP) and for antiviral and cytostatic activity. (C) 2013 Elsevier Ltd. All rights reserved.
ISSN: 0040-4020
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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