title: Syntheses and biological studies of novel spiropiperazinyl oxazolidinone antibacterial agents using a spirocyclic diene derived acylnitroso Diels-Alder reaction.
abstract: Several novel oxazolidinone antibiotics with a spiropiperazinyl substituent at the 4'-position of the phenyl ring were synthesized through nitroso Diels-Alder chemistry and the in vitro antibacterial activities were evaluated against various Gram-positive bacteria (Bacillus subtilis, Staphylococcus aureus, Enterococcus faecalis), Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa) and mycobacteria (Mycobacterium vaccae, Mycobacterium tuberculosis). Analogs (8a and 12) were active against selected drug resistant microbes, like methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) and had no mammalian toxicity in a Hep-2 cellular assay (CC(50) >100 μM).
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA.
authors.forename: Cheng
authors.initials: C
authors.lastname: Ji
authors.forename: Weimin
authors.initials: W
authors.lastname: Lin
authors.forename: Garrett C
authors.initials: GC
authors.lastname: Moraski
authors.forename: Jane A
authors.initials: JA
authors.lastname: Thanassi
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Pucci
authors.forename: Scott G
authors.initials: SG
authors.lastname: Franzblau
authors.forename: Ute
authors.initials: U
authors.lastname: Möllmann
authors.forename: Marvin J
authors.initials: MJ
authors.lastname: Miller
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology*; D002460:Cell Line; D004353:Drug Evaluation, Preclinical / Q000379:methods; D024881:Drug Resistance, Bacterial; D016983:Enterococcus / Q000187:drug effects; D013293:Enterococcus faecalis / Q000187:drug effects; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006801:Humans; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009161:Mycobacterium / Q000187:drug effects; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects; D014640:Vancomycin / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D023303:Oxazolidinones; D014640:Vancomycin