Design, Synthesis and Biological Evaluation of N-Sulfonyl Homoserine Lactone Derivatives as Inhibitors of Quorum Sensing in Chromobacterium violaceum

A novel series of N-sulfonyl homoserine lactone derivatives 5a–l has been designed, synthesized and evaluated for quorum sensing inhibitory activities towards violacein production. Of the compounds synthesized, compound 5h was found to possess an excellent level of enantiopurity (99.2% e.e.). The re...

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Detalles Bibliográficos
Autores principales: Zhao, Mingming, Yu, Yingying, Hua, Yuhui, Feng, Fan, Tong, Yigang, Yang, Xiaohong, Xiao, Junhai, Song, Hongrui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270181/
https://www.ncbi.nlm.nih.gov/pubmed/23486105
http://dx.doi.org/10.3390/molecules18033266
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author Zhao, Mingming
Yu, Yingying
Hua, Yuhui
Feng, Fan
Tong, Yigang
Yang, Xiaohong
Xiao, Junhai
Song, Hongrui
author_facet Zhao, Mingming
Yu, Yingying
Hua, Yuhui
Feng, Fan
Tong, Yigang
Yang, Xiaohong
Xiao, Junhai
Song, Hongrui
author_sort Zhao, Mingming
collection PubMed
description A novel series of N-sulfonyl homoserine lactone derivatives 5a–l has been designed, synthesized and evaluated for quorum sensing inhibitory activities towards violacein production. Of the compounds synthesized, compound 5h was found to possess an excellent level of enantiopurity (99.2% e.e.). The results indicated that compounds bearing an ortho substituent on their phenyl ring exhibited excellent levels of inhibitory activity against violacein production. Compounds 5h and 5k in particular, with IC(50) values of 1.64 and 1.66 µM, respectively, were identified as promising lead compounds for further structural modification.
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spelling pubmed-62701812018-12-20 Design, Synthesis and Biological Evaluation of N-Sulfonyl Homoserine Lactone Derivatives as Inhibitors of Quorum Sensing in Chromobacterium violaceum Zhao, Mingming Yu, Yingying Hua, Yuhui Feng, Fan Tong, Yigang Yang, Xiaohong Xiao, Junhai Song, Hongrui Molecules Article A novel series of N-sulfonyl homoserine lactone derivatives 5a–l has been designed, synthesized and evaluated for quorum sensing inhibitory activities towards violacein production. Of the compounds synthesized, compound 5h was found to possess an excellent level of enantiopurity (99.2% e.e.). The results indicated that compounds bearing an ortho substituent on their phenyl ring exhibited excellent levels of inhibitory activity against violacein production. Compounds 5h and 5k in particular, with IC(50) values of 1.64 and 1.66 µM, respectively, were identified as promising lead compounds for further structural modification. MDPI 2013-03-13 /pmc/articles/PMC6270181/ /pubmed/23486105 http://dx.doi.org/10.3390/molecules18033266 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Zhao, Mingming
Yu, Yingying
Hua, Yuhui
Feng, Fan
Tong, Yigang
Yang, Xiaohong
Xiao, Junhai
Song, Hongrui
Design, Synthesis and Biological Evaluation of N-Sulfonyl Homoserine Lactone Derivatives as Inhibitors of Quorum Sensing in Chromobacterium violaceum
title Design, Synthesis and Biological Evaluation of N-Sulfonyl Homoserine Lactone Derivatives as Inhibitors of Quorum Sensing in Chromobacterium violaceum
title_full Design, Synthesis and Biological Evaluation of N-Sulfonyl Homoserine Lactone Derivatives as Inhibitors of Quorum Sensing in Chromobacterium violaceum
title_fullStr Design, Synthesis and Biological Evaluation of N-Sulfonyl Homoserine Lactone Derivatives as Inhibitors of Quorum Sensing in Chromobacterium violaceum
title_full_unstemmed Design, Synthesis and Biological Evaluation of N-Sulfonyl Homoserine Lactone Derivatives as Inhibitors of Quorum Sensing in Chromobacterium violaceum
title_short Design, Synthesis and Biological Evaluation of N-Sulfonyl Homoserine Lactone Derivatives as Inhibitors of Quorum Sensing in Chromobacterium violaceum
title_sort design, synthesis and biological evaluation of n-sulfonyl homoserine lactone derivatives as inhibitors of quorum sensing in chromobacterium violaceum
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270181/
https://www.ncbi.nlm.nih.gov/pubmed/23486105
http://dx.doi.org/10.3390/molecules18033266
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