title: (2,3)-alpha-Methylenepenams: synthesis and in vitro activity.
abstract: A series of alpha-methylene penicillins was synthesized and SAR were studied. The alpha-isomers were found to be chemically reactive and biologically active in contrast to the beta-isomers. In addition, the alpha-isomers have broader spectrum of in vitro activity than the corresponding penicillins. Generally, the alpha-isomers are more active against gram-negative bacteria than the corresponding penicillins, but slightly weaker in potency towards gram-positive organisms.
authors.affiliation: Roche Research Center, Nutley, NJ 07110.
authors.forename: C C
authors.initials: CC
authors.lastname: Wei
authors.forename: K C
authors.initials: KC
authors.lastname: Luk
authors.forename: K F
authors.initials: KF
authors.lastname: West
authors.forename: J L
authors.initials: JL
authors.lastname: Roberts
authors.forename: D
authors.initials: D
authors.lastname: Pruess
authors.forename: D W
authors.initials: DW
authors.lastname: Moore
authors.forename: R
authors.initials: R
authors.lastname: Yang
authors.forename: T
authors.initials: T
authors.lastname: Steppe
authors.forename: P
authors.initials: P
authors.lastname: Rossman
authors.forename: M
authors.initials: M
authors.lastname: Weigele
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001426:Bacterial Proteins; D002352:Carrier Proteins / Q000378:metabolism; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006602:Hexosyltransferases; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D002267:Muramoylpentapeptide Carboxypeptidase / Q000378:metabolism; D010400:Penicillin G / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D046915:Penicillin-Binding Proteins; D010406:Penicillins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010458:Peptidyl Transferases; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D001426:Bacterial Proteins; D002352:Carrier Proteins; D046915:Penicillin-Binding Proteins; D010406:Penicillins; C054982:2,3-methylene penam; D010458:Peptidyl Transferases; D006602:Hexosyltransferases; D002267:Muramoylpentapeptide Carboxypeptidase; D010400:Penicillin G