Synthesis of zwitterionic N-chlorohydantoins for antibacterial applications. Issue 23 (15th December 2018)

• Record Type: Journal Article
• Authors: Li, Lingdong; Jin, Yanan; Zhou, Hao; Wang, Hande
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 28:Issue 23/24(2018)
• Page Start: 3665
• Page End: 3669
• Publication Date: 2018-12-15
• Subjects: N-chlorohydantoins -- Zwitterionic compounds -- Chemical synthesis -- Antibacterial application; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2018.10.034
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Highlights: A carboxybetaine N -chlorohydantoins and a sulfobetaine N -chlorohydantoins were synthesized. The carboxybetaine N -chlorohydantoins displayed satisfactory antimicrobial efficacy. Biocidal activity of synthetic N -chlorohydantoins depends on the nature of zwitterionic head group. Abstract: Two novel zwitterionic N- chlorohydantoin biocides, containing an N- chlorohydantoin unit and a sulfobetaine unit or a carboxybetaine unit, were chemically synthesized and characterized. Using the quaternary ammonium N- chlorohydantoin as control, the antibacterial activity of synthetic zwitterionic N- chlorohydantoins was challenged and the antibacterial data showed that carboxybetaine N- chlorohydantoin exhibited distinctively higher biocidal efficacy than QA counterpart, while sulfobetaine N- chlorohydantoin displayed slightly inferior antimicrobial efficacy. Our results may inspire further exploration of more zwitterionic N- chlorohydantoin analogs for antibacterial application.