35975-71-4

Usage

Uses

Used in Pharmaceutical Industry:
8-Chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid is used as a broad-spectrum antibiotic for the treatment of various bacterial infections. Its mechanism of action involves the inhibition of bacterial DNA gyrase and topoisomerase IV enzymes, which are essential for the replication and repair of bacterial DNA. This action effectively disrupts the bacteria's ability to reproduce and repair itself, leading to their elimination from the body. The broad-spectrum nature of this antibiotic makes it a valuable asset in the treatment of a wide range of bacterial infections, offering a versatile solution for combating various pathogens.

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Evaluation of 3-carboxy-4(1H)-quinolones as inhibitors of human protein kinase CK2

Due to the emerging role of protein kinase CK2 as a molecule that participates not only in the development of some cancers but also in viral infections and inflammatory failures, small organic inhibitors of CK2, besides application in scientific research, may have therapeutic significance. In this paper, we present a new class of CK2 inhibitors-3-carboxy-4(1H)-quinolones. This class of inhibitors has been selected via receptor-based virtual screening of the Otava compound library. It was revealed that the most active compounds, 5,6,8-trichloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (7) (IC 50 = 0.3 μM) and 4-oxo-1,4-dihydrobenzo[h]quinoline-3-carboxylic acid (9) (IC50 = 1 μM), are ATP competitive (Ki values are 0.06 and 0.28 μM, respectively). Evaluation of the inhibitors on seven protein kinases shows considerable selectivity toward CK2. According to theoretical calculations and experimental data, a structural model describing the key features of 3-carboxy-4(1H)-quinolones responsible for tight binding to CK2 active site has been developed.