Synthesis and antibacterial activity of 1-oxacephem derivatives.

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Abstract
A number of new optically active 1-oxacephem compounds were synthesized and tested for antibacterial activity. Various 7.alpha.-unsubstituted 1-oxacephem nuclei and a 7.alpha.-methoxy-1-oxacephem nucleus, reported previously, were converted into the corresponding phenylacetylamino-, 2-thienylacetylamino-, D-mandelylamino-, D-phenylglycylamino- and arylmalonylamino-1-oxacephem carboxylic acids. All the compounds except for the phenylglycylamino derivatives exhibited 4-16-fold enhanced antibacterial activity compared with that of the corresponding cephalosporins. A combination of the 7.alpha.-methoxy-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-1-oxacephem nucleus and a 7.beta.-arylmalonylamino side chain, as represented by compound 1, produced the highest efficacy among them: high antibacterial activity with a widely expanded spectrum against gram-negative bacteria including resistant strains and Pseudomonas aeruginosa was observed.