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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
Jain, Prashi Li, Jiaqin Porubsky, Patrick R. Neuenswander, Benjamin Egan, Susan M. Aubé, Jeffrey Rogers, Steven A.
Jain, Prashi
Li, Jiaqin
Porubsky, Patrick R.
Neuenswander, Benjamin
Egan, Susan M.
Aubé, Jeffrey
Rogers, Steven A.
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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.
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2014-08-18
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Royal Society of Chemistry
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Jain, P., Li, J., Porubsky, P., Neuenswander, B., Egan, S. M., Aubé, J., & Rogers, S. (2014). 3-Substituted Biquinolinium Inhibitors of AraC Family Transcriptional Activator VirF from S. flexneri Obtained Through In Situ Chemical Ionization of 3,4-Disubstituted Dihydroquinolines. RSC Advances, 4(75), 39809–39816. http://doi.org/10.1039/C4RA08384A