103995-01-3

Usage

Uses

Used in Pharmaceutical Industry:
1-(2,4-Difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid is used as a key intermediate in the synthesis of hydrazinoquinolones and azetidinylquinolinones derivatives. These derivatives possess potent antibacterial properties, making them valuable in the development of new antibiotics to combat drug-resistant bacterial strains.
1-(2,4-DIFLUOROPHENYL)-6,7-DIFLUORO-1,4-DIHYDRO-4-OXOQUINOLINE-3-CARBOXYLIC ACID's role in the synthesis of these derivatives is attributed to its ability to be modified and functionalized, allowing for the creation of molecules with enhanced antibacterial activity. Its unique structure and reactivity make it an essential component in the design and production of novel antimicrobial agents, addressing the growing need for effective treatments against resistant bacteria.

InChI:InChI=1/C16H7F4NO3/c17-7-1-2-13(12(20)3-7)21-6-9(16(23)24)15(22)8-4-10(18)11(19)5-14(8)21/h1-6H,(H,23,24)

Upstream product

• 108115-67-9 ethyl 3-(2,4-difluoroanilino)-2-(2,4,5-trifluorobenzoyl)acrylate 
• 129322-83-4 2',4',5'-trifluoroacetophenone 
• 88419-56-1 2,4,5-trifluorobenzoyl chloride 
• 367-23-7 1,2,4-trifluorobenzene 
• 98349-24-7 ethyl 2,4,5-trifluorobenzoylacetate 
• 446-17-3 2,4,5-trifluorobenzoic acid 
• 367-25-9 2,4-difluorophenylamine 
• 108138-17-6 6,7-difluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid ethyl ester 

Downstream Products

• 132233-66-0 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(3-ethylaminomethyl-1-pyrrolidinyl)quinoline-3-carboxylic acid 
• 108138-27-8 A 57531 
• 174358-28-2 PD 161654 
• 141725-88-4 cetefloxacin 
• 145122-52-7 1-(2,4-difluorophenyl)-6-fluoro-7-(3,3-dimethylpiperazin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride 
• 138808-67-0 1-(2,4-Difluoro-phenyl)-6-fluoro-7-((1S,4S)-5-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 130982-86-4 (R)-(+)-temafloxacin 

Relevant academic research and scientific papers

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.

Synthesis, Antibacterial Activities, and Pharmacological Properties of Enantiomers of Temafloxacin Hydrochloride

Temafloxacin hydrochloride is a potent member of the 4-pyridone-3-carboxylic acid class of antibacterial agents and is currently under clinical development as a broad-spectrum antimicrobial agent.It is a racemate having a chiral center at the C3 of the 7-piperazin-1-yl group.The two enantiomers were synthesized and tested for their antibacterial activities.Although no difference in in vitro antibacterial activities was observed, a minor difference in in vivo antibacterial activities was observed.However, they both exhibited similar pharmacological profiles.