title: Syntheses and antibacterial activity studies of new oxazolidinones from nitroso Diels-Alder chemistry.
abstract: A series of novel oxazolidinone antibiotics having [2.2.1] and [2.2.2] bicyclic oxazine moieties at the C-5 side chain of the A-ring was synthesized by nitroso Diels-Alder reactions, from three linezolid analogs containing morpholine, piperazine and thiomorpholine, respectively, as the C-ring components. Subsequent N-O bond cleavage generated oxazolidinones with 4-amino cyclo-2-en-1-ol substituents. The in vitro antibacterial activities of these oxazolidinone analogs were evaluated.
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA.
authors.forename: Shanshan
authors.initials: S
authors.lastname: Yan
authors.forename: Marvin J
authors.initials: MJ
authors.lastname: Miller
authors.forename: Timothy A
authors.initials: TA
authors.lastname: Wencewicz
authors.forename: Ute
authors.initials: U
authors.lastname: Möllmann
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006094:Gram-Positive Bacteria / Q000187:drug effects / Q000502:physiology; D008826:Microbial Sensitivity Tests; D009603:Nitroso Compounds / Q000737:chemistry*; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D009603:Nitroso Compounds; D023303:Oxazolidinones