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Molecules 2017, 22(12), 2090; doi:10.3390/molecules22122090

2-Substituted Aniline as a Simple Scaffold for LuxR-Regulated QS Modulation

1
Univ Lyon, INSA LYON, Université Lyon 1, CPE Lyon, UMR 5246, CNRS, ICBMS, Bât. J. Verne, 20 Avenue A. Einstein, F-69621 Villeurbanne, France
2
Univ Lyon, INSA Lyon, Université Lyon 1, UMR 5240, CNRS, MAP, 10 rue Raphaël Dubois, F-69622 Villeurbanne, France
*
Authors to whom correspondence should be addressed.
Received: 29 September 2017 / Revised: 17 November 2017 / Accepted: 27 November 2017 / Published: 29 November 2017
(This article belongs to the Special Issue Design and Synthesis of Quorum-Sensing Inhibitors)
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Abstract

The ability of the 2-substituted aniline motif to serve as a scaffold for designing potential LuxR-regulated quorum sensing (QS) modulators has been investigated, using docking experiments and biological evaluation of a series of 15 specially synthesized compounds. Aniline, 2-acetyl-aniline and 2-nitroaniline were considered, as well as their N-acylated derivatives. Docking experiments showed that the 2-substituted aniline motif fits within the LuxR binding site at the place of the lactone moiety of AHL, and the biological evaluation revealed QS antagonisitic activity for several compounds, validating the hypothesis that this scaffold acts on QS. Structure activity relationships are discussed regarding interactions with the key residues of the LuxR binding site, showing significant variations in the H-bonding pattern. View Full-Text
Keywords: quorum sensing; antagonists; 2-nitroaniline scaffold; molecular docking quorum sensing; antagonists; 2-nitroaniline scaffold; molecular docking
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Li, S.; Wawrzyniak, J.; Queneau, Y.; Soulère, L. 2-Substituted Aniline as a Simple Scaffold for LuxR-Regulated QS Modulation. Molecules 2017, 22, 2090.

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