Section 42
Chapter 41,525

Synthetic cephalosporins. IV. Synthesis and antibacterial activity of 7 beta-[ (Z) -2- (2-aminothiazol-4-yl) -2- (O-substituted oxyimino) acetamido]-3- (1,2,3-triazol-1-yl) methyl-3-cephem-4-carboxylic acid and related compounds

Sakagami, K.; Sakai, M.; Kashi, T.; Ishimaru, T.

Yakugaku Zasshi Journal of the Pharmaceutical Society of Japan 109(12): 957-961


ISSN/ISBN: 0031-6903
PMID: 2630639
DOI: 10.1248/yakushi1947.109.12_957
Accession: 041524143

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Synthesis and oral activity of 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-(O-substituted oxyimino)-acetamido]-3-(1,2,3-triazol-1-yl)methyl-3-cephem-4 -carboxylic acid and its related compounds were described. 3-(1,2,3-Triazol-1-yl)methylcephalosporins have been prepared by the direct cycloaddition of acetylene to 3-azidomethylcephalosporins, which were obtained by nucleophilic substitution of 3-chloromethylcephalosporins with sodium azide in N,N-dimethylformamide. The cephalosporins (8a--c) had potent and wide antibacterial spectra against gram positive and gram negative bacteria which were comparable to those of cefixime or cefteram. Urinary recovery of 9a and 9b, pivaloyloxymethyl esters of 8a and 8b, were 9.2% and 3.5%, respectively, through oral administration in mice, exhibiting lower rate than that of cefteram pivoxyl (28%).

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