title: 5,6-Cis-penems: broad-spectrum anti-methicillin-resistant Staphylococcus aureus beta-lactam antibiotics.
abstract: 5,6-cis-Penem derivatives have been synthesized and evaluated as anti-MRSA antibiotics. The cis-penems 5 and 6 showed potent activities against not only MRSA but also a wide variety of bacteria including beta-lactamase-producing microorganisms. These compounds were designed to have high affinity to the penicillin-binding protein 2a of MRSA and to form stable acyl intermediates with beta-lactamases by blocking the deacylating water molecule.
authors.affiliation: Suntory Institute for Bioorganic Research, Institute for Biomedical Research, Osaka, Japan.
authors.forename: M
authors.initials: M
authors.lastname: Ishiguro
authors.forename: R
authors.initials: R
authors.lastname: Tanaka
authors.forename: K
authors.initials: K
authors.lastname: Namikawa
authors.forename: T
authors.initials: T
authors.lastname: Nasu
authors.forename: H
authors.initials: H
authors.lastname: Inoue
authors.forename: T
authors.initials: T
authors.lastname: Nakatsuka
authors.forename: Y
authors.initials: Y
authors.lastname: Oyama
authors.forename: S
authors.initials: S
authors.lastname: Imajo
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007202:Indicators and Reagents; D007769:Lactams; D009682:Magnetic Resonance Spectroscopy; D016106:Methicillin Resistance; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013211:Staphylococcus aureus / Q000187:drug effects* / Q000235:genetics; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D047090:beta-Lactams
chemical_list: C106948:2-((1-phenacylpyrrolidin-3-yl)thio)-6-(1-hydroxypropyl)penem-3-carboxylic acid; C106947:2-((pyrrolidin-3-yl)thio)-6-(1-hydroxypropyl)penem-3-carboxylic acid; D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; D007769:Lactams; D047090:beta-Lactams