Issue 4, 2013
From the journal:

MedChemComm

5′-Nor carbocyclic nucleosides: unusual nonnucleoside inhibitors of HIV-1 reverse transcriptase†

Elena S. Matyugina,a   Vladimir T. Valuev-Elliston,a   Denis A. Babkov,b   Mikhail S. Novikov,b   Alexander V. Ivanov,a   Sergey N. Kochetkov,a   Jan Balzarini,c   Katherine L. Seley-Radtke*d  and  Anastasia L. Khandazhinskaya*a  

* Corresponding authors

a Engelhardt Institute of Molecular Biology, Russian Academy of Science, Vavilov Str., 32, Moscow 119991, Russia
E-mail: khandazhinskaya@bk.ru

b Department of Pharmaceutical & Toxicological Chemistry, Volgograd State Medical University, Pavshikh Bortsov Sq., 1, Volgograd 400131, Russia

c Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, Leuven B-3000, Belgium

d Department of Chemistry & Biochemistry, University of Maryland, Baltimore County, 1000 Hilltop Circle, Baltimore, MD 21250, USA
E-mail: kseley@umbc.edu

Abstract

A new series of potential nonnucleoside inhibitors of HIV-1 reverse transcriptase (NNRTIs) based on the carbocyclic 5′-nor-uracil scaffold were designed and synthesized. Binding modes in the active site of the enzyme were studied computationally to provide insight on potential interactions. Several of the 2′,3′-dideoxy-2′,3′-didehydro-5′-nor-uridine analogues showed inhibitory activity against wild-type and mutant (L100I) HIV-RT with Ki 13–18 μM and 1–11 μM, respectively.

Graphical abstract: 5′-Nor carbocyclic nucleosides: unusual nonnucleoside inhibitors of HIV-1 reverse transcriptase

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Article information

DOI
https://doi.org/10.1039/C3MD00036B
Article type
Concise Article
Submitted
03 Feb 2013
Accepted
05 Mar 2013
First published
06 Mar 2013

Med. Chem. Commun., 2013,4, 741-748

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5′-Nor carbocyclic nucleosides: unusual nonnucleoside inhibitors of HIV-1 reverse transcriptase

E. S. Matyugina, V. T. Valuev-Elliston, D. A. Babkov, M. S. Novikov, A. V. Ivanov, S. N. Kochetkov, J. Balzarini, K. L. Seley-Radtke and A. L. Khandazhinskaya, Med. Chem. Commun., 2013, 4, 741 DOI: 10.1039/C3MD00036B

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