103994-99-6

Usage

Uses

Used in Pharmaceutical Industry:
6,7-Difluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid is used as an intermediate in the synthesis of antibacterial agents for the treatment of bacterial infections. Its unique structure and fluorine-containing nature contribute to its enhanced activity against various bacterial strains, making it a valuable component in the development of new antimicrobial drugs.
Used in Research and Development:
In addition to its pharmaceutical applications, 6,7-Difluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid is also utilized in research and development for the study of arylfluoroquinoline chemistry and its potential applications in other fields, such as materials science or agrochemicals. Its unique properties and reactivity make it an interesting subject for further exploration and innovation.

Upstream product

• 108138-16-5 1-(p-fluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid ethyl ester 
• 108115-66-8 ethyl 3-(4-fuoroanilino)-2-(2,4,5-trifuorobenzoyl)acrylate 
• 98349-24-7 ethyl 2,4,5-trifluorobenzoylacetate 
• 446-17-3 2,4,5-trifluorobenzoic acid 

Downstream Products

• 138698-26-7 7-(1,4-Diaza-bicyclo[3.3.1]non-4-yl)-6-fluoro-1-(4-fluoro-phenyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 112894-29-8 1-(4-fluorophenyl)-6-fluoro-1,4-dihydro-7-(1,4-diazabicyclo[3.2.2]non-4-yl)-4-oxo-3-quinoline carboxylic acid 
• 138698-14-3 6-Fluoro-1-(4-fluoro-phenyl)-7-(9-methyl-3,9-diaza-bicyclo[4.2.1]non-3-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 98105-99-8 sarafloxacin 
• 138808-69-2 1-(4-Fluorophenyl)-6-fluoro-1,4-dihydro-7-{(1S_.4S)-2,5-diazabicyclo[2.2.1]hept-2-yl}-4-oxo-3-quinolinecarboxylic acid 
• 108437-27-0 6-Fluoro-1-(4-fluorophenyl)-1,4-dihydro-7(8-methyl-3,8-diazabicyclo(3.2.1)oct-3-yl)-4-oxoquinoline-3-carboxylic acid 
• 98106-29-7 6-Fluoro-1-(4-fluoro-phenyl)-7-morpholin-4-yl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 98106-17-3 difloxacin 
• 138808-75-0 6-Fluoro-1-(4-fluoro-phenyl)-7-((1S,4S)-5-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 123187-96-2 1-(4-fluorophenyl)-6-fluoro-7-<3-(fluoromethyl)-1-piperazinyl>-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 

Relevant academic research and scientific papers

Synthesis of norfloxacin analogues catalyzed by Lewis and Br?nsted acids: An alternative pathway

An alternative synthetic pathway to prepare norfloxacin analogues is presented. Three Lewis acids (CeCl3·7H2O, AlCl 3·6H2O, ZnCl2) and one Bro?nsted acid (TsOH) were tested as catalysts in the prepara

Synthesis of [1-15N,2-13C]-labeled difloxacin

The synthesis of [1-15N,2-13C]-difloxacin, an arylfluoroquinolone antibacterial agent, is reported. As a crucial initial step, the starting materials ethyl 2,4,5-trifluorobenzoylacetate, [formyl- 13C]-triethyl orthoformate, and [15N]-4-fluoroaniline were reacted to ethyl [15N,3-13C]-3-(4-fluoroanilino)-2-(2,4, 5-trifluorobenzoyl)acrylate. After cyclization and ester cleavage, the resulting intermediate was reacted with 1-methylpiperazine to [1-15N,2- 13C]-1-(4-fluorophenyl)-6-fluoro-7-(4-methyl-1-piperazinyl)-1, 4-dihydro-4-oxoquinoline-3-carboxylate, i.e., [1-15N,2- 13C]-difloxacin. The overall yield was 62% based on the non-labeled and 43% based on the labeled starting materials (both used in 1.4 molar excess). The product was identified by 1H-, 13C-, and 15N-NMR spectroscopy and by cochromatography (TLC, HPLC) with an authentic reference; its purity (HPLC) was above 98%. Prior to synthesis of [1-15N,2-13C]-difloxacin, non-labeled difloxacin was synthesized in order to optimize procedures and to identify and characterize all intermediates.

Baylis-Hillman route to several quinolone antibiotic intermediates

Treatment of methyl propiolate and 2,4,5-trifluoro-, 2-fluoro-, 2-fluoro-5-methoxy- or 2,3,4,5-tetrafluorobenzaldehydes with a ZrCl 4/Bu4NI combination induces an aldol reaction to furnish β-iodo-α-(hydroxyalkyl)acrylates. These can be used for the preparation of several quinolone intermediates, 1-substituted 4-oxo-1,4-dihydroquinoline-3-carboxylic acids and 9,10-difluoro-3-methyl-2,3- dihydro-7-oxo-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid through the oxidation, amination and hydrolysis reactions. Georg Thieme Verlag Stuttgart.

Effect of Lipophilicity at N-1 on Activity of Fluoroquinolones against Mycobacteria

The dramatic increase in drug resistant Mycobacterium tuberculosis has caused a resurgence in research targeted toward these organisms.As part of a systematic study to optimize the quinolone antibacterials against mycobacteria, we have prepared a series of N-1-phenyl-substituted derivatives to explore the effect of increasing lipophilicity on potency at this position.The compounds, synthesized by the modification of a literature procedure, were evaluated for activity against Gram-negative and Gram-positive bacteria, Mycobacterium fortuitum and Mycobacterium smegmatis, and the results correlated with log P, pKa, and other attributes.The activity of the compounds against the rapidly growing, less hazardous organism M. fortuitum was used as a measure of M. tuberculosis activity.The results demonstrate that increasing lipophilic character by itself does not correlate with increased potency against mycobacteria.Rather, intrinsic activity against Gram-negative and/or Gram-positive bacteria is the governing factor for corresponding activity against mycobacteria.

Heterocycylic-substituted quinoline-carboxylic acids

1-Substituted-6-fluoro-7-heterocyclic-1,4-dihydroquino-1-(or dihydronaphthyridin)-4-one carboxylic acids have antibacterial properties. The 7-heterocyclic group is a bicyclic group, one of the rings of which is saturated and the other ring of which is unsaturated.