title: Design, synthesis and biological evaluation of N-sulfonyl homoserine lactone derivatives as inhibitors of quorum sensing in Chromobacterium violaceum.
abstract: 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.
authors.affiliation: School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe District, Shenyang 110016, China. zhaomingmingbest@163.com
authors.forename: Mingming
authors.initials: M
authors.lastname: Zhao
authors.forename: Yingying
authors.initials: Y
authors.lastname: Yu
authors.forename: Yuhui
authors.initials: Y
authors.lastname: Hua
authors.forename: Fan
authors.initials: F
authors.lastname: Feng
authors.forename: Yigang
authors.initials: Y
authors.lastname: Tong
authors.forename: Xiaohong
authors.initials: X
authors.lastname: Yang
authors.forename: Junhai
authors.initials: J
authors.lastname: Xiao
authors.forename: Hongrui
authors.initials: H
authors.lastname: Song
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D020134:Catalytic Domain; D002861:Chromobacterium / Q000187:drug effects* / Q000378:metabolism; D007211:Indoles / Q000378:metabolism; D062105:Molecular Docking Simulation; D011487:Protein Conformation; D053038:Quorum Sensing / Q000187:drug effects*
chemical_list: D000900:Anti-Bacterial Agents; D007211:Indoles; C088386:homoserine lactone; D015107:4-Butyrolactone; C063155:violacein