US EPA

7431169 

Journal Article 

Dual-action cephalosporins: cephalosporin 3'-quinolone carbamates 

Albrecht, HA; Beskid, G; Christenson, JG; Georgopapadakou, NH; Keith, DD; Konzelmann, FM; Pruess, DL; Rossman, PL; Wei, CC; , 

1991 

Yes 

Journal of Medicinal Chemistry
ISSN: 0022-2623
EISSN: 1520-4804 

AMER CHEMICAL SOC 

WASHINGTON 

34 

9 

2857-2864 

English 

1910090 

10.1021/jm00113a026 

WOS:A1991GF10300026 

https://pubs.acs.org/doi/abs/10.1021/jm00113a026
Exit
 

A series of cephalosporins has been prepared in which the 3'-position was linked to the nitrogen of the antibacterial quinolone ciprofloxacin through a carbamate function. Like the ester-linked and quaternary-linked dual-action cephalosporins reported earlier, these carbamate-linked compounds exhibited a broad antibacterial spectrum derived from both cephalosporin-like and quinolone-like activities, suggesting a dual mode of action. Studies to elucidate details of the mechanism of action have been inconclusive. Ciprofloxacin liberated as a consequence of bacterial enzyme-mediated reactions may contribute to the second mode of action, although some evidence indicates that the intact carbamate-linked bifunctional molecules may possess intrinsically both beta-lactam and quinolone activities. 

7 [2 (2 amino 4 thiazolyl) 2 (methoxyimino)acetamido] 3 [[[[4 (3 carboxy 1 cyclopropyl 6 fluoro 1,4 dihydro 4 oxo 7 quinolyl)piperazinyl]carbonyl]oxy]methyl] 3 cephem 4 carboxylic acid; cefotaxime; ceftazidime; cephalosporin derivative; ciprofloxacin; ciprofloxacin derivative; penicillin binding protein; penicillin g; quinoline derivative; ro 24 4383; unclassified drug; antibacterial activity; article; dna synthesis; drug metabolism; drug protein binding; drug synthesis; escherichia coli; gram negative bacterium; gram positive bacterium; in vitro study; minimum inhibitory concentration; nonhuman; priority journal; structure activity relation; Animal; Anti-Infective Agents; Carbamates; Cefotaxime; Cephalosporins; Chromatography, High Pressure Liquid; Ciprofloxacin; Escherichia coli; Mice; Pseudomonas aeruginosa; Spectrophotometry, Infrared; Staphylococcus aureus; Streptococcus pneumoniae