35975-71-4

Basic information

• Product Name: 8-Chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• Synonyms: 3-quinolinecarboxylic acid, 8-chloro-1,4-dihydro-4-oxo-; 3-quinolinecarboxylic acid, 8-chloro-4-hydroxy-; 8-Chloro-4-hydroxyquinoline-3-carboxylic acid; 4-Hydroxy-8-chloroquinoline-3-carboxylicacid; 4-Hydroxy-8-chloroquinoline-3-carboxylic acid; 4-Hydroxy-8-chloroquinoline-3-caroboxylic acid
• CAS NO: 35975-71-4
• Molecular Formula: C₁₀H₆ClNO₃
• Molecular Weight: 223.6125
• Mol File: 35975-71-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 393°C at 760 mmHg
• Flash Point: 191.5°C
• Density: 1.549g/cm³
• Vapor Pressure: 7E-07mmHg at 25°C
• Refractive Index: 1.648
• CAS DataBase Reference: 8-Chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid(35975-71-4)
• EPA Substance Registry System: 8-Chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid(35975-71-4)

Safety Data

• Hazardous Substances Data: 35975-71-4(Hazardous Substances Data)

Usage

General Description

8-Chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid is a chemical compound that belongs to the quinolone class of antibiotics. It is a synthetic derivative of quinoline and has a chloro and carboxylic acid functional group attached to the quinoline ring. 8-Chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid has been studied for its antibacterial activity and is used in the treatment of various bacterial infections. It works by inhibiting the bacterial DNA gyrase and topoisomerase IV enzymes, thus preventing the replication and repair of bacterial DNA. Its structure and mechanism of action make it an effective broad-spectrum antibiotic, making it useful in treating a wide range of bacterial infections.

Upstream product

• 52980-27-5 8-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 
• 95-51-2 o-chloroaniline 
• 19056-78-1 2-[(2-chlorophenylamino)-methylene]-malonic acid diethyl ester 

Downstream Products

• 1351945-13-5 1-methyl-4-oxo-3-((2-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)carbamoyl)-1,4-dihydroquinoline-8-carboxylic acid 
• 1351945-12-4 8-(aminomethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-3-quinolinecarboxamide 
• 1351945-11-3 8-(2-hydroxyethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)-1,4-dihydroquinoline-3-carboxamide 
• 1351945-38-4 1-methyl-4-oxo-8-(2-oxoethyl)-N-(2-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)-1,4-dihydroquinoline-3-carboxamide 
• 1351945-31-7 8-formyl-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenyl-4-yl)-1,4-dihydro-3-quinolinecarboxamide 
• 1351945-08-8 8-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)-1,4-dihydroquinoline-3-carboxamide 
• 1351945-30-6 8-(1,2-dihydroxyethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-3-quinolinecarboxamide 
• 1351945-29-3 8-ethenyl-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-3-quinolinecarboxamide 
• 1351945-28-2 8-chloro-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-3-quinolinecarboxamide 

Relevant articles and documents

Design, synthesis, and biological evaluation of novel arylcarboxamide derivatives as anti-tubercular agents

Our group has previously reported several indolecarboxamides exhibiting potent antitubercular activity. Herein, we rationally designed several arylcarboxamides based on our previously reported homology model and the recently published crystal structure of the mycobacterial membrane protein large 3 (MmpL3). Many analogues showed considerable anti-TB activity against drug-sensitive (DS) Mycobacterium tuberculosis (M. tb) strain. Naphthamide derivatives 13c and 13d were the most active compounds in our study (MIC: 6.55, 7.11 μM, respectively), showing comparable potency to the first line anti-tuberculosis (anti-TB) drug ethambutol (MIC: 4.89 μM). In addition to the naphthamide derivatives, we also identified the quinolone-2-carboxamides and 4-arylthiazole-2-carboxamides as potential MmpL3 inhibitors in which compounds 8i and 18b had MIC values of 9.97 and 9.82 μM, respectively. All four compounds retained their high activity against multidrug-resistant (MDR) and extensively drug-resistant (XDR) M. tb strains. It is worth noting that the two most active compounds 13c and 13d also exhibited the highest selective activity towards DS, MDR and XDR M. tb strains over mammalian cells [IC50 (Vero cells) ≥ 227 μM], indicating their potential lack of cytotoxicity. The four compounds were docked into the MmpL3 active site and were studied for their drug-likeness using Lipinski's rule of five.