Studies on pyridonecarboxylic acids. IV. Synthesis and antibacterial activity evaluation of S-(-)- and R-(+)-6-fluoro-1-methyl 4-oxo-7-(1-piperazinyl) 4H-[1,3]thiazeto[3,2-a]quinol ine-3-carboxylic acids

Optically active isomers of 6-fluoro-1-methyl 4-oxo-7-(1-piperazinyl) 4H-[1,3]thiazeto[3,2-a]quinoline 3- carboxylic acid (NM394, 3) were prepared through optical resolution of their racemic intermediate ( plus or minus )-1 by high-performance liquid chromatography (HPLC). The absolute configuration...

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Published inChemical & pharmaceutical bulletin Vol. 43; no. 7; pp. 1238 - 1240
Main Authors Segawa, J, Kazuno, K, Matsuoka, M, Amimoto, I, Ozaki, M, Matsuda, M, Tomii, Y, Kitano, M, Kise, M
Format Journal Article
LanguageEnglish
Published 01.01.1995
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Summary:Optically active isomers of 6-fluoro-1-methyl 4-oxo-7-(1-piperazinyl) 4H-[1,3]thiazeto[3,2-a]quinoline 3- carboxylic acid (NM394, 3) were prepared through optical resolution of their racemic intermediate ( plus or minus )-1 by high-performance liquid chromatography (HPLC). The absolute configuration at the C-1 position in the thiazeto-quinolone ring of (-)-3 was confirmed by X-ray analysis of (-)-4 to be S. The in vitro antibacterial activity of (-)-3 was 2-8 times that of (+)-3.
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ISSN:0009-2363