Issue 1, 2012
From the journal:

Organic & Biomolecular Chemistry

Synthesis and in vitro enzymatic and antiviral evaluation of phosphoramidate d4T derivatives as chain terminators

Shiqiong Yang,a   Christophe Pannecouque,b   Eveline Lescrinier,a   Anne Girauta  and  Piet Herdewijn*a  

* Corresponding authors

a Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, Leuven, Belgium
E-mail: piet.herdewijn@rega.kuleuven.ac.be
Fax: +32 16 337340
Tel: +32 16 337387

b Department of Microbiology and Immunology, Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, Leuven, Belgium

Abstract

The anti-HIV activity of nucleoside analogues is highly related to their substrate specificity for cellular and viral kinase and, as triphosphate, for HIV-RT. A series of phosphoramidate d4T derivatives have been synthesized and evaluated as substrates for HIV-1 RT, and also tested for their in vitro anti-HIV activity. Compounds 2 and 4 are able to inhibit HIV-1 replication to the same extent as d4T and d4TMP in MT-4 cells as well as in CEM/0 cells and CEM/TK−cells. The data suggests that these phosphoramidates are hydrolysed to d4T before exerting their antiviral activity.

Graphical abstract: Synthesis and in vitro enzymatic and antiviral evaluation of phosphoramidate d4T derivatives as chain terminators

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Article information

DOI
https://doi.org/10.1039/C1OB06214J
Article type
Paper
Submitted
20 Jul 2011
Accepted
22 Sep 2011
First published
08 Nov 2011

Org. Biomol. Chem., 2012,10, 146-153

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Synthesis and in vitro enzymatic and antiviral evaluation of phosphoramidate d4T derivatives as chain terminators

S. Yang, C. Pannecouque, E. Lescrinier, A. Giraut and P. Herdewijn, Org. Biomol. Chem., 2012, 10, 146 DOI: 10.1039/C1OB06214J

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