Section 42
Chapter 41,525

Synthetic cephalosporins. V. Synthesis and antibacterial activity of 3-alkylthio-7 beta-[ (Z) -2- (2-aminothiazol-4-yl) -2- (O-substituted oxyimino) acetamido]cephalosporins and related compounds

Sakagami, K.; Watanabe, T.; Fukatsu, S.; Nitta, H.; Hatanaka, M.; Ishimaru, T.

Yakugaku Zasshi Journal of the Pharmaceutical Society of Japan 109(12): 913-925


ISSN/ISBN: 0031-6903
PMID: 2698417
DOI: 10.1248/yakushi1947.109.12_913
Accession: 041524144

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3-Alkylthio-7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-(O-substituted oxyimino)acetamido]cephalosporins (6 and 7) and the 3-methoxy analogues (10) were prepared by coupling diphenylmethyl 7-amino-3-alkylthio-3-cephem-4-carboxylate (1 and 2) or diphenylmethyl 7-amino-3-methoxy-3-cephem-4-carboxylate with (Z)-2-(2-tritylaminothiazol-4-yl)-2-(O-substituted oxyimino)acetic acid (4), followed by deprotection and subjected to examination of antibacterial activities. The pivaloyloxymethyl esters (8 and 9) of the compounds (6 and 7) were also prepared and oral activities of these esters were compared with those of the parent compounds (6 and 7). The cephalosporins (6a-j and 7a-c) had potent and wide antibacterial spectra against Gram positive and Gram negative bacteria which were comparable to those of cefixime or cefteram. Among them, the cephalosporins (6f and 7c) and the pivaloyloxymethyl esters (8b and 9b) had good in vivo efficacy in mice against infections of Escherichia coli No. 29 and especially 8b showed high urinary recovery in mice.

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