108138-27-8

Basic information

• Product Name: 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
• CAS NO: 108138-27-8
• Molecular Formula: C₂₀H₁₆F₃N₃O₃
• Molecular Weight: 403.3545
• Mol File: 108138-27-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 611°C at 760 mmHg
• Flash Point: 323.3°C
• Density: 1.48g/cm³
• Vapor Pressure: 8.74E-16mmHg at 25°C
• Refractive Index: 1.62
• CAS DataBase Reference: 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid(108138-27-8)
• EPA Substance Registry System: 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid(108138-27-8)

Safety Data

• Hazardous Substances Data: 108138-27-8(Hazardous Substances Data)

Usage

Description

1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid is a complex chemical compound with a quinoline core, featuring a carboxylic acid functional group and fluorine and piperazine substituents attached to the aromatic rings. It is a significant building block in medicinal chemistry and belongs to the class of fluoroquinolone antibiotics.

Uses

Used in Pharmaceutical Industry:
1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid is used as an active pharmaceutical ingredient for the development of potent antibacterial agents. Its unique chemical structure provides high potency and broad-spectrum activity against various clinically relevant bacterial pathogens.
Used in Antimicrobial Applications:
As a fluoroquinolone antibiotic, 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid is employed for the treatment of a wide range of bacterial infections. It works by inhibiting bacterial DNA gyrase and topoisomerase IV, which are essential for bacterial DNA replication, ultimately leading to bacterial cell death.
Used in Research and Development:
1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid serves as a valuable compound in the research and development of new antibiotics and pharmaceuticals. Its complex molecular structure allows for the exploration of various modifications and improvements to enhance its antibacterial properties and overcome resistance issues.

Upstream product

• 110-85-0 piperazine 
• 103995-01-3 6,7-difluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-3-quinoline-carboxylic acid 
• 367-25-9 2,4-difluorophenylamine 
• 446-17-3 2,4,5-trifluorobenzoic acid 
• 98349-24-7 ethyl 2,4,5-trifluorobenzoylacetate 
• 108138-17-6 6,7-difluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid ethyl ester 
• 108115-67-9 ethyl 3-(2,4-difluoroanilino)-2-(2,4,5-trifluorobenzoyl)acrylate 
• 98105-93-2 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid 

Relevant articles and documents

Synthesis, molecular docking and biological evaluation of quinolone derivatives as novel anticancer agents

A series of novel quinolone derivatives (8a-j) were synthesized, and their anticancer activities were tested in human cancer cell lines, human lung carcinoma cell (A549), human promyelocytic leukemia cell (HL-60), and human cervical cancer cell (Hela). Compound 8i was found to be 5-times more potent in cellkilling activity for cell lines A549, HL-60, and Hela than the positive control irinotecan or cisplatin, with IC50 of 0.009, 0.008 and 0.010 μM, respectively. The docking study revealed that compound 8i might have strong interactions with the active site of DNA-topoisomerase I.

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.