title: 6 alpha-hydroxypenicillanic acid-S(S)-oxide and analogues: synthesis and antimicrobial activity.
abstract: The synthesis and in vitro antibacterial activity of a series of 6-oxygenated penicillanic acid sulfoxides is described. 6 alpha-Hydroxypenicillanic acid-S(S)-oxide (1a) exhibits weak Gram-negative antibacterial activity and appears to be similar to amdinocillin (5) in its mode of action. 6 alpha-Hydroxypenicillanic acid-S(R)-oxide (4a) has a broader spectrum of activity, but again is rather weak. The corresponding 6 beta-hydroxy series is essentially devoid of activity.
authors.affiliation: Roche Research Center, Hoffmann-La Roche Inc., Nutley, New Jersey 07110.
authors.forename: J L
authors.initials: JL
authors.lastname: Roberts
authors.forename: P F
authors.initials: PF
authors.lastname: Bevilacqua
authors.forename: D D
authors.initials: DD
authors.lastname: Keith
authors.forename: B A
authors.initials: BA
authors.lastname: Pawson
authors.forename: D L
authors.initials: DL
authors.lastname: Pruess
authors.forename: P L
authors.initials: PL
authors.lastname: Rossman
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects*; D010397:Penicillanic Acid / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D010397:Penicillanic Acid