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Issue 14, 2002
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Synthesis and antiviral evaluation of novel conformationally locked nucleosides and masked 5′-phosphate derivatives thereof

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Abstract

As part of a programme towards evaluating the potential of conformationally locked 3′-deoxy- and 3′-azido-3′-deoxy-nucleoside derivatives as prodrugs of potential 5′-O-triphosphorylated anti-HIV drugs, novel nucleoside derivatives with locked N-type (north-type, C3′-endo) furanose conformation were prepared using convergent synthetic strategies. In addition, masked 5′-monophosphate derivatives of these, and of a conformationally restricted 3′-azido-3′-deoxynucleoside with E-type (eastern-type, O4′-endo) furanose conformation, were prepared in order to potentially circumvent the first phosphorylation step. However, neither the free 5′-hydroxy derivatives nor the masked 5′-monophosphates showed anti-HIV activity in MT-4 cells.

Graphical abstract: Synthesis and antiviral evaluation of novel conformationally locked nucleosides and masked 5′-phosphate derivatives thereof

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Article information


Submitted
09 Apr 2002
Accepted
31 May 2002
First published
19 Jun 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1655-1662
Article type
Paper

Synthesis and antiviral evaluation of novel conformationally locked nucleosides and masked 5′-phosphate derivatives thereof

T. Bryld, M. H. Sørensen, P. Nielsen, T. Koch, C. Nielsen and J. Wengel, J. Chem. Soc., Perkin Trans. 1, 2002, 1655
DOI: 10.1039/B203484K

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