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

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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Bibliographic Details
Main Authors: Junhai Xiao, Yigang Tong, Xiaohong Yang, Fan Feng, Yuhui Hua, Yingying Yu, Mingming Zhao, Hongrui Song
Format: Article
Language:English
Published: MDPI AG 2013-03-01
Series:Molecules
Subjects:
N-sulfonyl homoserine lactone
quorum sensing inhibitor
design
synthesis
Online Access:http://www.mdpi.com/1420-3049/18/3/3266
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spelling doaj-5c3029abbfcb4e9f9f94e6e22dbda0122020-11-24T22:43:52ZengMDPI AGMolecules1420-30492013-03-011833266327810.3390/molecules18033266Design, Synthesis and Biological Evaluation of N-Sulfonyl Homoserine Lactone Derivatives as Inhibitors of Quorum Sensing in Chromobacterium violaceumJunhai XiaoYigang TongXiaohong YangFan FengYuhui HuaYingying YuMingming ZhaoHongrui SongA 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 IC50 values of 1.64 and 1.66 µM, respectively, were identified as promising lead compounds for further structural modification.http://www.mdpi.com/1420-3049/18/3/3266N-sulfonyl homoserine lactonequorum sensing inhibitordesignsynthesis
collection DOAJ
language English
format Article
sources DOAJ
author Junhai Xiao
Yigang Tong
Xiaohong Yang
Fan Feng
Yuhui Hua
Yingying Yu
Mingming Zhao
Hongrui Song
spellingShingle Junhai Xiao
Yigang Tong
Xiaohong Yang
Fan Feng
Yuhui Hua
Yingying Yu
Mingming Zhao
Hongrui Song
Design, Synthesis and Biological Evaluation of N-Sulfonyl Homoserine Lactone Derivatives as Inhibitors of Quorum Sensing in Chromobacterium violaceum
Molecules
N-sulfonyl homoserine lactone
quorum sensing inhibitor
design
synthesis
author_facet Junhai Xiao
Yigang Tong
Xiaohong Yang
Fan Feng
Yuhui Hua
Yingying Yu
Mingming Zhao
Hongrui Song
author_sort Junhai Xiao
title 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_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_sort design, synthesis and biological evaluation of n-sulfonyl homoserine lactone derivatives as inhibitors of quorum sensing in chromobacterium violaceum
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2013-03-01
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 IC50 values of 1.64 and 1.66 µM, respectively, were identified as promising lead compounds for further structural modification.
topic N-sulfonyl homoserine lactone
quorum sensing inhibitor
design
synthesis
url http://www.mdpi.com/1420-3049/18/3/3266
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AT yuhuihua designsynthesisandbiologicalevaluationofnsulfonylhomoserinelactonederivativesasinhibitorsofquorumsensinginchromobacteriumviolaceum
AT yingyingyu designsynthesisandbiologicalevaluationofnsulfonylhomoserinelactonederivativesasinhibitorsofquorumsensinginchromobacteriumviolaceum
AT mingmingzhao designsynthesisandbiologicalevaluationofnsulfonylhomoserinelactonederivativesasinhibitorsofquorumsensinginchromobacteriumviolaceum
AT hongruisong designsynthesisandbiologicalevaluationofnsulfonylhomoserinelactonederivativesasinhibitorsofquorumsensinginchromobacteriumviolaceum
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