title: Highly Stereoselective Synthesis of Saccharin-Substituted β-Lactams via in Situ Generation of a Heterosubstituted Ketene and a Zwitterionic Intermediate as Potential Antibacterial Agents.
abstract: Highly stereoselective synthesis of saccharin derivatives containing functionalized 2-azetidinone moiety was achieved starting from saccharin as an available precursor. The approach to these valuable heterocyclic scaffolds involves a formal [2π + 2π] cycloaddition between Schiff bases and the saccharinylketene as a novel ketene which was generated in situ and an electrocyclic reaction of a zwitterionic intermediate. The identification of the ketene was confirmed by reaction with the stable free radical TEMPO (TO•). Also, the antimicrobial activities of some new substituted saccharin against nine standard bacteria, four bacteria which were isolated from clinical samples and one yeast, were evaluated.
authors.affiliation: †Department of Chemistry, Shahid Bahonar University of Kerman, 22 Bahman Avenue, 76169 Kerman, Iran.
authors.forename: Zahra F A
authors.initials: ZF
authors.lastname: Mortazavi
authors.affiliation: †Department of Chemistry, Shahid Bahonar University of Kerman, 22 Bahman Avenue, 76169 Kerman, Iran.
authors.forename: Mohammad R
authors.initials: MR
authors.lastname: Islami
authors.affiliation: ‡Department of Biology, Shahid Bahonar University of Kerman, 76169 Kerman, Iran.
authors.forename: Moj
authors.initials: M
authors.lastname: Khaleghi
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D061565:Cycloaddition Reaction; D005030:Ethylenes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D012439:Saccharin / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012545:Schiff Bases; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D005030:Ethylenes; D007659:Ketones; D012545:Schiff Bases; D047090:beta-Lactams; D012439:Saccharin; C008223:ketene