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Issue 75, 2014
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3-Substituted biquinolinium inhibitors of AraC family transcriptional activator VirF from S. flexneri obtained through in situ chemical ionization of 3,4-disubstituted dihydroquinolines

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Abstract

During a structure–activity relationship optimization campaign to develop an inhibitor of AraC family transcriptional activators, we discovered an unexpected transformation of a previously reported inhibitor that occurs under the assay conditions. Once placed in the assay media, the 3,4-disubstituted dihydroquinoline core of the active analogue rapidly undergoes a decomposition reaction to a quaternary 3-substituted biquinolinium. Further examination established an SAR for this chemotype while also demonstrating its resilience to irreversible binding of biologically relevant nucleophiles.

Graphical abstract: 3-Substituted biquinolinium inhibitors of AraC family transcriptional activator VirF from S. flexneri obtained through in situ chemical ionization of 3,4-disubstituted dihydroquinolines

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Publication details

The article was received on 10 Jul 2014, accepted on 18 Aug 2014 and first published on 18 Aug 2014


Article type: Paper
DOI: 10.1039/C4RA08384A
Citation: RSC Adv., 2014,4, 39809-39816
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    3-Substituted biquinolinium inhibitors of AraC family transcriptional activator VirF from S. flexneri obtained through in situ chemical ionization of 3,4-disubstituted dihydroquinolines

    P. Jain, J. Li, P. Porubsky, B. Neuenswander, S. M. Egan, J. Aubé and S. Rogers, RSC Adv., 2014, 4, 39809
    DOI: 10.1039/C4RA08384A

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