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
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%).