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Journal of Antimicrobial Chemotherapy (1987) 19, 753-760
© 1987 The British Society for Antimicrobial Chemotherapy

research-article

Structure-activity relations of 4-fluoromethyl monobactams

Kouji Matsudaa,*, Susumu Nakagawac, Fumio Nakanoc, Matsuhisa Inoueb and Susumu Mitsuhashia

aEpisome Institute Fujimimura, Seta-gun, Gunma bLaboratory of Drug Resistance in Bacteria, Gunma University, School of Medicine Gunma cOkazaki Research Laboratories, Banyu Pharmaceutical Co., Ltd. Okazaki, Japan

accepted 9 December 1986

*Banyu Pharmaceutical Co. Ltd. Central Research Lab., 3-9-1 Kamimutsune, Okazaki, Aichi 444, Japan.

New monobactam compounds with fluoromethyl side chains at the 4-position were synthesized. These compounds showed strong antibacterial activity against Gram-negative bacteria including Pseudomonas aeruginosa and good stability to various ß-lactamases.

The effect of replacement of the 1-carboxy-1-methylethoxyimino residue of aztreonam with various substituted groups, and of the configuration of the 3- and 4-position were examined.

Substitution of a carboxycyclopropoxy group in the oxyimino moiety effected the most potent antibacterial activity. The cis congeners were not hydrolysed by any types of ß-lactamases including the oxyiminocephalosporin hydrolysing enzyme. Introduction of a fluorine atom in the methyl group at the 4-position increased the ß-lactamase stability of monobactams.


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