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Issue 15, 2017
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Stereoselective synthesis of novel adamantane derivatives with high potency against rimantadine-resistant influenza A virus strains

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Abstract

A series of (R)- and (S)-isomers of new adamantane-substituted heterocycles (1,3-oxazinan-2-one, piperidine-2,4-dione, piperidine-2-one and piperidine) with potent activity against rimantadine-resistant strains of influenza A virus were synthesized through the transformation of adamantyl-substituted N-Boc-homoallylamines 8 into piperidine-2,4-diones 11 through the cyclic bromourethanes 9 and key intermediate enol esters 10. Biological assays of the prepared compounds were performed on the rimantadine-resistant S31N mutated strains of influenza A – A/California/7/2009(H1N1)pdm09 and modern pandemic strain A/IIV-Orenburg/29-L/2016(H1N1)pdm09. The most potent compounds were both enantiomers of the enol ester 10 displaying IC50 = 7.7 μM with the 2016 Orenburg strain.

Graphical abstract: Stereoselective synthesis of novel adamantane derivatives with high potency against rimantadine-resistant influenza A virus strains

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Publication details

The article was received on 11 Feb 2017, accepted on 10 Mar 2017 and first published on 10 Mar 2017


Article type: Communication
DOI: 10.1039/C7OB00331E
Citation: Org. Biomol. Chem., 2017,15, 3152-3157
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    Stereoselective synthesis of novel adamantane derivatives with high potency against rimantadine-resistant influenza A virus strains

    N. Yu. Kuznetsov, R. M. Tikhov, I. A. Godovikov, M. G. Medvedev, K. A. Lyssenko, E. I. Burtseva, E. S. Kirillova and Y. N. Bubnov, Org. Biomol. Chem., 2017, 15, 3152
    DOI: 10.1039/C7OB00331E

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