Jump to main content
Jump to site search

Issue 15, 2017
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

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
  • Open access: Creative Commons BY license
  •   Request permissions

    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

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements