title: 6-(substituted methylene)penems, potent broad spectrum inhibitors of bacterial beta-lactamase. III. Structure-activity relationships of the 5-membered heterocyclic derivatives.
abstract: Sodium (5RS)-Z-6-(heterocyclylmethylene)penem-3-carboxylates (2) are a series of extremely potent inhibitors of bacterial beta-lactamases. A variety of 5-membered heteroaromatic derivatives have been prepared and structure-activity studies reveal a preferred substituent orientation. One of these derivatives, the 1-methyl-1,2,3-triazolyl compound (5m) is a more potent synergist of amoxycillin than clavulanic acid, sulbactam or tazobactam.
authors.affiliation: Smith Kline Beecham Pharmaceuticals, Chemotherapeutic Research Centre, Surrey, UK.
authors.forename: I
authors.initials: I
authors.lastname: Bennett
authors.forename: N J
authors.initials: NJ
authors.lastname: Broom
authors.forename: G
authors.initials: G
authors.lastname: Bruton
authors.forename: S
authors.initials: S
authors.lastname: Calvert
authors.forename: B P
authors.initials: BP
authors.lastname: Clarke
authors.forename: K
authors.initials: K
authors.lastname: Coleman
authors.forename: R
authors.initials: R
authors.lastname: Edmondson
authors.forename: P
authors.initials: P
authors.lastname: Edwards
authors.forename: D
authors.initials: D
authors.lastname: Jones
authors.forename: N F
authors.initials: NF
authors.lastname: Osborne
mesh_terms: D000658:Amoxicillin / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects* / Q000201:enzymology; D004357:Drug Synergism; D008968:Molecular Conformation; D013329:Structure-Activity Relationship; D065093:beta-Lactamase Inhibitors
chemical_list: D000900:Anti-Bacterial Agents; D065093:beta-Lactamase Inhibitors; D000658:Amoxicillin