Studies on β-Lactam Antibiotics. V. Synthesis of 6-[D (-)-α-(Acylamino)-4-hydroxyphenylacetamido] penicillanic Acids and Antibacterial Activity

1 January 1980

journal article
research article
Published by Pharmaceutical Society of Japan in YAKUGAKU ZASSHI

Vol. 100 (2) , 133-139
https://doi.org/10.1248/yakushi1947.100.2_133

Abstract

6-[D(-)-.alpha.-(Acylamino)-4-hydroxyphenylacetamido]penicillanic acids (1-12) were prepared by reacting amoxicillin with the active esters of nitrogen-containing heterocyclic compounds (11). These penicillins were tested for in vitro activities against Staphylococcus aureus, Escherchia coli, Klebsiella pneumoniae, Proteus mirabilis and Pseudomonas aeruginosa. Structure-activity relationships were discussed. The 4-hydroxyquinoline derivative (5) and the 4-hydroxy-1,5-naphthyridine derivatives (8-11) have potent antibacterial activity against E. coli, K. pneumoniae, P. mirabilis and P. aeruginosa. Among the penicillins tested, sodium 6-[D(-)-.alpha.-(4-hydroxy-1,5-naphthyridine-3-carboxamido)-4-hydroxyphenylacetamido]penicillanate (8) exhibited the highest activity against P. aeruginosa, its MIC [minimal inhibitory concentration] being 1.56 .mu.g/ml.

Keywords

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Studies on quinoline derivatives and related compounds. III. A novel pyridine synthesis to give substituted 1,4‐dihydro‐4‐oxonicotinic acids
Journal of Heterocyclic Chemistry, 1975