258879-74-2Relevant academic research and scientific papers
Synthesis and antibacterial activity of novel 7-substituted-6-fluoro-1- fluoromethyl-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid derivatives
Matsuoka, Masato,Segawa, Jun,Amimoto, Isao,Masui, Yasushi,Tomii, Yoshifumi,Kitano, Masahiko,Kise, Masahiro
, p. 1765 - 1773 (2007/10/03)
A series of 7-substituted-6-fluoro-1-fluoromethyl-4-oxo-4H- [1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid derivatives (2a - I) was prepared and evaluated for antibacterial activity. These compounds were obtained by deacylation of 4-benzoyloxy-2-(1-chloro-2-fluoroethyl)thio-6,7- difluoroquinoline-3-carboxylate (10) and subsequent intramolecular cyclization followed by substitution with cyclic amines and then hydrolysis. The intramolecular cyclization reaction of 18, one of the diastereomers (17, 18) revealed that the cyclization reaction proceeded through an inversion to afford (-)-11a in good chemical and optical yield. The enantiomers of 2a were prepared from the enantiomers of 11a, which were obtained by the optical resolution of the racemate using high-performance liquid chromatography (HPLC). Compounds 2a,b showed excellent in vitro and in vivo antibacterial activity against both gram-negative and gram-positive bacteria including quinolone and Methicillin-resistant Staphylococcus aureus.
OPTICALLY ACTIVE QUINOLINECARBOXYLIC ACID DERIVATIVE AND PROCESS FOR PRODUCING THE SAME
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, (2008/06/13)
This invention provides a process for producing compound [Ia] and [Ib] which comprises reacting compound [III] with a chiral carboxylic acid or amino acid, or a reactive derivative thereof, reacting the resulting compound [II] with a chlorinating agent, and separating diastereomers from the resulting diastereomer mixture. wherein R1typically represents hydrogen or halogen; R2typically represents hydrogen; R3typically represents alkyl; R4represents chiral acyl or amino residue; X represents halogen, substituted or unsubstituted cyclic amino, or phenyl.
