Section 42
Chapter 41,329

Semisynthetic beta-lactam antibiotics. IV. Synthesis and antibacterial activity of 7 beta-[2- (hetero aromatic methoxyimino) -2- (2-aminothiazol-4-yl) acetamido]cephalosporins

Arimoto, M.; Yokohama, S.; Sudou, M.; Ichikawa, Y.; Hayano, T.; Tagawa, H.; Furukawa, M.

Journal of Antibiotics 41(12): 1795-1811


ISSN/ISBN: 0021-8820
PMID: 3209474
DOI: 10.7164/antibiotics.41.1795
Accession: 041328857

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A series of 7 beta-[2-(hetero aromatic methoxyimino)-2-(2-aminothiazol-4-yl)acetamido]- cephalosporins have been synthesized and bacteriologically evaluated. Several substances in this series showed exceptional in vitro activity, especially those with a five-membered hetero aromatic substituent moiety at the 7-position and a quaternary ammonium group as the 3-function of the cephem nucleus. The most active derivative, 7 beta-[2-(imidazol-4-ylmethoxyimino)-2-(2-aminothiazol-4-yl)a cetamido]-3-(pyridiniomethyl)ceph-3-em-4-carboxylate (13a) was the most evenly balanced with respect to activity against Gram-positive and Gram-negative bacteria. Furthermore, 13 was stable to various types of beta-lactamases and had high affinities for penicillin binding protein-3 and -1Bs of both Escherichia coli and Pseudomonas aeruginosa.

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