title: Hetacillin (R)- and (S)-sulfoxides. Synthesis and structure-activity relationships.
abstract: Hetacillin was oxidized with m-chloroperbenzoic acid to give the corresponding (R)- and (S)-sulfoxides. Ozonization of hetacillin not only oxidized the sulfide but caused unexpected oxidation of the imidazolidine ring to a 2H-imidazoline. The biological spectrum showed the (R)-sulfoxide to be appreciably more active than the (S)-sulfoxide.
mesh_terms: D000818:Animals; D051379:Mice; D008826:Microbial Sensitivity Tests; D010406:Penicillins / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D013237:Stereoisomerism; D013290:Streptococcal Infections / Q000188:drug therapy; D013297:Streptococcus pyogenes; D013329:Structure-Activity Relationship; D013454:Sulfoxides / Q000138:chemical synthesis / Q000494:pharmacology / Q000627:therapeutic use
chemical_list: D010406:Penicillins; D013454:Sulfoxides