Section 44
Chapter 43,740

New broad-spectrum cephalosporins with anti-pseudomonal activity. II. Synthesis and antibacterial activity of 7 beta-[2-acylamino-2- (4-hydroxyphenyl) acetamido]-3-[ (1-methyl-1H-tetrazol-5-yl) thiomethyl]ceph-3-em-4-carboxylic acids

Yamada, H.; Tobiki, H.; Jimpo, K.; Gooda, K.; Takeuchi, Y.; Ueda, S.; Komatsu, T.; Okuda, T.; Noguchi, H.; Irie, K.; Nakagome, T.

Journal of Antibiotics 36(5): 532-542


ISSN/ISBN: 0021-8820
PMID: 6409869
DOI: 10.7164/antibiotics.36.532
Accession: 043739483

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The influence of the chirality of the 7-acyl side chain and of various N-acyl moieties (A-CO-) on the in vitro activity of 7 beta-[2-acylamino-2-(4-hydroxyphenyl)acetamido ]-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]ceph-3-em-4-carboxylic acids (6) was investigated. A cephalosporin having a 7-acyl side chain of S-configuration (6r) was only weakly active against Staphylococcus aureus and Klebsiella pneumoniae and was inactive against the other species tested. Among the various N-acyl moieties in the cephalosporins having a 7-acyl side chain of the R-configuration, the 4-hydroxypyridine-3-carbonyl moiety, unsubstituted or substituted with 5-bromo and/or 6-alkyl groups and the 4-hydroxy-1,5-naphthyridine-3-carbonyl moiety, unsubstituted or substituted with a 6-methyl and a 6-methoxy group gave the most active compounds. N-Ethylation of the 4-hydroxy-1,5-naphthyridine-3-carbonyl derivative and the 4-hydroxypyridine-3-carbonyl derivative (6p, 6q) resulted in a decrease of the in vitro activity.

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