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]quinoline-3-carboxylic acids.
Optically active isomers of 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H- [1,3] thiazeto [3,2-alpha] quinoline-3- carboxylic acid (NM394, 3) were prepared through optical resolution of their racemic intermediate ( +/- )-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 ( - )-4 to be S. The in vitro antibacterial activity of ( - )-3 was 2--8 times that of (+)-3.
Segawa
J
J
Chemistry Laboratory, Nippon Shinyaku Company, Ltd., Kyoto, Japan.
Kazuno
K
K
Matsuoka
M
M
Amimoto
I
I
Ozaki
M
M
Matsuda
M
M
Tomii
Y
Y
Kitano
M
M
Kise
M
M
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001412:Bacillus subtilis / Q000187:drug effects; D018360:Crystallography, X-Ray; D004926:Escherichia coli / Q000187:drug effects; D024841:Fluoroquinolones; D008826:Microbial Sensitivity Tests; D010879:Piperazines / Q000138:chemical synthesis* / Q000494:pharmacology*; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D015363:Quinolones / Q000138:chemical synthesis* / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000890:Anti-Infective Agents; D024841:Fluoroquinolones; D010879:Piperazines; D015363:Quinolones; C074190:ulifloxacin