New broad-spectrum cephalosporins with anti-pseudomonal activity. I. Synthesis and antibacterial activity of 7.Beta.- (D-2- ( (4-hydroxy-1,5-naphthyridine-3-carbonylamino) - and (4-hydroxypyridine-3-carbonylamino) ) -2- (4-hydoxyphenyl) acetamido) cephalosporins

Yamada, H.; Jimpo, K.; Tobiki, H.; Komatsu, T.; Noguchi, H.; Irie, K.; Nakagome, T.

The Journal of Antibiotics 36(5): 522-531


DOI: 10.7164/antibiotics.36.522
Accession: 068516094

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The synthesis and the antibacterial activity of 7 beta-[D-2-[(4-hydroxy-1,5-naphthyridine-3-carbonylamino)- and (4-hydroxypyridine-3-carbonylamino)]-2-(4-hydroxyphenyl)acetamido]-cephalosporins with various substituents at the 3-position in the cephem nucleus are described. These compounds exhibited strong antibacterial activities against a variety of Gram-positive and Gram-negative bacteria, including Pseudomonas aeruginosa and Enterobacter aerogenes, which are insensitive to cefazolin and cefmetazole. The compounds (3e, 4e) having a 1-methyl-1H-tetrazolylthiomethyl group at the 3-position appeared to show the best activity in each series. The 4-hydroxypyridine-3-carbonylamino derivative 4e gave higher peak serum concentrations and urinary recovery rates than those of the 4-hydroxy-1,5-naphthyridine derivative 3e when administered subcutaneously to mice and intramuscularly to rats.