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.

Keywords

• N-sulfonyl homoserine lactone
• quorum sensing inhibitor
• design
• synthesis