ORALLY ACTIVE CEPHALOSPORINS II. SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF NEW 7β-[(<i>Z</i>)-2-(2-AMINOTHIAZOL-4-YL)-2-HYDROXYIMINOACETAMIDO]-CEPHALOSPORINS WITH 1, 2, 3-TRIAZOLE IN C-3 SIDE CHAIN

MASAHARU KUME; TADATOSHI KUBOTA; YASUO KIMURA; HIROMU NAKASHIMIZU; KIYOSHI MOTOKAWA; MASAO NAKANO

doi:10.7164/antibiotics.46.177

ORALLY ACTIVE CEPHALOSPORINS

II. SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF NEW 7β-[(Z)-2-(2-AMINOTHIAZOL-4-YL)-2-HYDROXYIMINOACETAMIDO]-CEPHALOSPORINS WITH 1, 2, 3-TRIAZOLE IN C-3 SIDE CHAIN

MASAHARU KUME, TADATOSHI KUBOTA, YASUO KIMURA, HIROMU NAKASHIMIZU, KIYOSHI MOTOKAWA, MASAO NAKANO

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JOURNAL FREE ACCESS

1993 Volume 46 Issue 1 Pages 177-192

DOI https://doi.org/10.7164/antibiotics.46.177

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Abstract

The synthesis, antibacterial activity and oral absorbability of 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(1H-1, 2, 3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid (1g) and related compounds are described. Their oral absorbability was influenced by the spacer length between C-3 of a cephem nucleus and C-4' of 1, 2, 3-triazole. The SCH₂S structure was also found to contribute to their good oral absorption. The quantitative relationship between the bioavailability and the spacer length of cephalosporins (1a-1n) is discussed.

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