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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
dc.contributor.author | Jain, Prashi | |
dc.contributor.author | Li, Jiaqin | |
dc.contributor.author | Porubsky, Patrick R. | |
dc.contributor.author | Neuenswander, Benjamin | |
dc.contributor.author | Egan, Susan M. | |
dc.contributor.author | Aubé, Jeffrey | |
dc.contributor.author | Rogers, Steven A. | |
dc.date.accessioned | 2017-05-31T16:00:52Z | |
dc.date.available | 2017-05-31T16:00:52Z | |
dc.date.issued | 2014-08-18 | |
dc.identifier.citation | 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 | en_US |
dc.identifier.uri | http://hdl.handle.net/1808/24316 | |
dc.description.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. | en_US |
dc.publisher | Royal Society of Chemistry | en_US |
dc.rights | This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License 4.0 (CC BY-NC-ND 4.0), which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made. | en_US |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | en_US |
dc.title | 3-Substituted biquinolinium inhibitors of AraC family transcriptional activator VirF from S. flexneri obtained through in situ chemical ionization of 3,4-disubstituted dihydroquinolines | en_US |
dc.type | Article | en_US |
kusw.kuauthor | Jain, Prashi | |
kusw.kuauthor | Li, Jiaqin | |
kusw.kuauthor | Porubsky, Patrick | |
kusw.kuauthor | Neuenswander, Benjamin | |
kusw.kuauthor | Egan, Susan M. | |
kusw.kuauthor | Aubé, Jeffrey | |
kusw.kuauthor | Rogers, Steven | |
kusw.kudepartment | Molecular Biosciences | en_US |
dc.identifier.doi | 10.1039/c4ra08384a | en_US |
dc.identifier.orcid | https://orcid.org/0000-0003-1049-5767 | |
kusw.oaversion | Scholarly/refereed, publisher version | en_US |
kusw.oapolicy | This item meets KU Open Access policy criteria. | en_US |
dc.identifier.pmid | PMC4170738 | en_US |
dc.rights.accessrights | openAccess |
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Except where otherwise noted, this item's license is described as: This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License 4.0 (CC BY-NC-ND 4.0), which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.