title: Synthesis of a new series of cephalosporins having 3-substituted-ammonio-1-propenyl group as the C-3 side chain.
abstract: The synthesis and antimicrobial activity of eight derivatives of 7-[(Z)-2-(2-aminothiazol-4-yl)- and 7-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido] cephalosporins having an (E) or (Z)-3-ammonio-1-propenyl group in the C-3 side chain are described. The (E)-propenyl derivatives were more active than their corresponding Z-isomers and showed well-balanced, broad antibacterial activity against both Gram-positive and Gram-negative bacteria including Pseudomonas aeruginosa.
authors.affiliation: Bristol-Myers Research Institute, Ltd., Tokyo Research Center, Japan.
authors.forename: H
authors.initials: H
authors.lastname: Kamachi
authors.forename: M
authors.initials: M
authors.lastname: Oka
authors.forename: Y
authors.initials: Y
authors.lastname: Narita
authors.forename: S
authors.initials: S
authors.lastname: Iimura
authors.forename: S
authors.initials: S
authors.lastname: Aburaki
authors.forename: H
authors.initials: H
authors.lastname: Yamashita
authors.forename: K
authors.initials: K
authors.lastname: Tomatsu
authors.forename: J
authors.initials: J
authors.lastname: Okumura
authors.forename: T
authors.initials: T
authors.lastname: Naito
mesh_terms: D001419:Bacteria / Q000187:drug effects; D002511:Cephalosporins / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D002511:Cephalosporins