84339-06-0Relevant 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.
Studies on pyridonecarboxylic acids. V. A practical synthesis of ethyl 6,7-difluoro-1-methyl-4-oxo-4H-[1,3]thiazeto[3,2-α]quinoline 3-carboxylate, a key intermediate for the new tricyclic quinolone, prulifloxacin (nm441) and versatile new syntheses of the 2-thioquinoline skeleton
Matsuoka,Segawa,Makita,Ohmachi,Kashima,Nakamura K.-,Hattori,Kitano,Kise
, p. 1773 - 1779 (2007/10/03)
A practical synthesis of ethyl 6,7-difluoro-1-methyl-4-oxo4H- [1,3]thiazeto[3,2-α]quinoline-3-carboxylate (9), the key intermediate for 6- fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl-1-piperazinyl]- 4-oxo-4H-[1,3]thiazeto[3,2-α]quinoline-3-carboxylic acid (2), NM441, was developed. The crucial points of this synthetic mute are the chlorination of ethyl 4-acetoxy-2-(ethylthio)-6,7-difluoroquinoline-3-carboxylate (12) and the subsequent deacetylation of the resulting 2-(1-chloroethyl)thio compound 13 followed by the intramolecular cyclization reaction. Versatile new syntheses of 2-thioquinoline skeleton were also developed. The first mute includes the intramolecular cyclization of the N,S-acetal 22 which was prepared from 2,4,5-trifluorobenzoic acid in three steps. The second one contains the regioselective attack of lithium enolate of ethyl acetate to the novel 2-(methylthio)-4H-[3,1]benzothiazine-4-one 29 at the 4-position followed by the intramolecular cyclization of the resulting β-ketoester 30.
7[4-(5 methyl-2-oxo-1,3-dioxalen-4-yl)methyl 1-piperzinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acids
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, (2008/06/13)
Quinolinecarboxylic acid derivatives of the formula (I) STR1 and pharmaceutically acceptable salts thereof, wherein R1 is hydrogen, straight or branch chain lower alkyl or phenyl unsubstituted or substituted by one or more halo moieties; R
STUDIES ON PYRIDONECARBOXYLIC ACIDS. 1. SYNTHESIS AND ANTIBACTERIAL EVALUATION OF 7-SUBSTITUTED-6-HALO-4-OXO-4H-THIAZETOQUINOLINE-3-CARBOXYLIC ACIDS
Segawa, Jun,Kitano, Masahiko,Kazuno, Kenji,Matsuoka, Masato,Shirahase, Ichiro,et al.
, p. 4727 - 4738 (2007/10/02)
A series of thiazetoquinoline-3-carboxylic acids and their esters were prepared and evaluated for antibacterial activity.The derivatives with a hydrogen or methyl group at C-1, fluorine at C-6, and piperazinyl or 4-methyl-1-piperazinyl group at C-7 showed superior in vitro antibacterial activity, and the derivatives with 4-methyl-1-piperazinyl group at C-7 had potent in vivo activity.Compound 29a (NM394) showed excellent in vitro antibacterial activity and low toxicity but poor absorption from the gastrointestinal tract.Compound 29ee (NM441), an N- derivative of 29a, was found to possess a favorable pharmacokinetic profile and oral activity superior to that of ciprofloxacin in experimental animals.
Substituted thiazetoquinoline-3-carboxylic acids and pharmaceutically acceptable salts thereof
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, (2008/06/13)
Anti-bacterial and anti-fungal compounds of formula I and pharmaceutically acceptable salts thereof: STR1 in which R1 is hydrogen, alkyl or substituted or unsubstituted phenyl; R2 is hydrogen, alkyl, alkoxy, hydroxy, halgen, nitro or substituted or unsubstituted amino; R3 is hydrogen or substituted or unsubstituted alkyl; R4 and R5 are the same or different and are alkyl or hydroxyalkyl or R4 and R5 together with the nitrogen atom to which they are attached form an unsubstituted or substituted heterocyclic ring having the depicted nitrogen atom as the sole heteroatom or which may have nitrogen, oxygen or sulphur atoms as additional heteroatoms; and X is halogen.
