52851-60-2

Usage

Uses

Used in Pharmaceutical Industry:
3-Quinolinecarboxylic acid, 1-ethyl-1,2-dihydro-4-hydroxy-2-oxo-, ethyl ester is used as an intermediate in the synthesis of pharmaceuticals for its ability to react with other compounds to form new medicinal agents.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Quinolinecarboxylic acid, 1-ethyl-1,2-dihydro-4-hydroxy-2-oxo-, ethyl ester is employed as an intermediate in the production of agrochemicals, contributing to the development of new pesticides or other agricultural products.
Used in Research and Development:
3-Quinolinecarboxylic acid, 1-ethyl-1,2-dihydro-4-hydroxy-2-oxo-, ethyl ester is used as a reactant in research and development for its potential to create new materials and compounds through chemical reactions with other substances.

InChI:InChI=1/C14H15NO4/c1-3-15-10-8-6-5-7-9(10)12(16)11(13(15)17)14(18)19-4-2/h5-8,18H,3-4H2,1-2H3/b14-11-

Upstream product

• 75-03-6 ethyl iodide 
• 169216-62-0 2-oxo-3-ethoxycarbonyl-4-acetoxyquinoline 
• 50332-68-8 N-ethylisatoic anhydride 
• 105-53-3 diethyl malonate 
• 118-48-9 isatoic anhydride 
• 6279-86-3 methanetricarboxylic acid triethyl ester 
• 103-69-5 N-ethyl-N-phenylamine 
• 118-92-3 anthranilic acid 
• 38446-21-8 ethyl 2-(ethylamino)benzoate 
• 99429-64-8 ethyl ester of 4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 
• 169216-65-3 ethyl 4-chloro-1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxylate 

Downstream Products

• 331963-43-0 C₁₉H₁₆FN₃O₄ 
• 331963-41-8 C₁₉H₁₇N₃O₄ 
• 331963-58-7 C₂₀H₁₉N₃O₄ 
• 331963-53-2 C₁₉H₁₆BrN₃O₄ 
• 303100-80-3 1-ethyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 4-bromoanilide 
• 84088-25-5 1-ethyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid anilide 
• 74693-62-2 1-ethyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid hydrazide 
• 331963-27-0 N'-dodecanoyl-1-ethyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbohydrazide 

Relevant academic research and scientific papers

4-Hydroxy-2-quinolones 127. Simple method for exchanging chlorine for hydroxyl in 1-R-4-chloro-3-ethoxycarbonyl-2-oxo-1,2-dihydroquinolines

Treatment of ethyl 1-R-4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylates with sodium nitrite in DMSO is a convenient method for their conversion to the corresponding 4-hydroxy derivatives.

Aryl or heteroaryl substituted thiadiazole compound and antibacterial application thereof

The invention belongs to the technical field of medicines, and particularly relates to an aryl or heteroaryl substituted thiadiazole compound, a preparation method and application thereof as an antibacterial drug. The compound is represented by formula (1

Discovery of 4-hydroxy-2-oxo-1,2-dihydroquinolines as potential inhibitors of Streptococcus pneumoniae, including drug-resistant strains

New therapies for treating drug-resistant pneumococcal infections are urgently needed. The novel scaffold 6-hydroxy-4-oxo-1,2-dihydro-4H-quinoline was shown to have similar efficacies against all three different serotypes of S. pneumoniae, ATCC 49617 (19F), ATCC BAA-1663 (15B), and ATCC 700904 (19A), in a resazurin-based high-throughput screen using the Korea Chemical Bank library. Further studies to identify a new lead with this scaffold, including tricyclic pyrrolo[3,2,1-ij]quinolone and pyrido[3,2,1-ij]quinolone derivatives, led to the identification of 6d, 7d and 12a. Compound 6d (IC50 = 0.92, 0.75, and 0.77 μM), 7d (IC50 = 0.57, 0.66, and 0.38 μM) and 12a (IC50 = 0.27, 1.03, and 0.62 μM) showed submicromolar IC50 values against 19F, 15B, and 19A, respectively, and thus serve as a starting point for further optimization. While some of compounds in this series exhibited acceptable pharmacokinetic profiles in preliminary in vivo rat experiments, the most active compound 12a showed poor solubility and high plasma protein binding. Our current research efforts are focused on optimizing compounds to improve physicochemical properties as well as potency.

N-thiadiazole-4-hydroxy-2-quinolone-3-carboxamides bearing heteroaromatic rings as novel antibacterial agents: Design, synthesis, biological evaluation and target identification

Due to the occurrence of antibiotic resistance, bacterial infectious diseases have become a serious threat to public health. To overcome antibiotic resistance, novel antibiotics are urgently needed. N-thiadiazole-4-hydroxy-2-quinolone-3-carboxamides are a potential new class of antibacterial agents, as one of its derivatives was identified as an antibacterial agent against S. aureus. However, no potency-directed structural optimization has been performed. In this study, we designed and synthesized 37 derivatives, and evaluated their antibacterial activity against S. aureus ATCC29213, which led to the identification of ten potent antibacterial agents with minimum inhibitory concentration (MIC) values below 1 μg/mL. Next, we performed bacterial growth inhibition assays against a panel of drug-resistant clinical isolates, including methicillin-resistant S. aureus, and cytotoxicity assays with HepG2 and HUVEC cells. One of the tested compounds named 1-ethyl-4-hydroxy-2-oxo-N-(5-(thiazol-2-yl)-1,3,4-thiadiazol-2-yl)-1,2-dihydroquinoline-3-carboxamide (g37) showed 2 to 128-times improvement compared with vancomycin in term of antibacterial potency against the tested strains (MICs: 0.25–1 μg/mL vs. 1–64 μg/mL) and an optimal selective toxicity (HepG2/MRSA, 110.6 to 221.2; HUVEC/MRSA, 77.6–155.2). Further, comprehensive evaluation indicated that g37 did not induce resistance development of MRSA over 20 passages, and it has been confirmed as a bactericidal, metabolically stable, orally active antibacterial agent. More importantly, we have identified the S. aureus DNA gyrase B as its potential target and proposed a potential binding mode by molecular docking. Taken together, the present work reports the most potent derivative of this chemical series (g37) and uncovers its potential target, which lays a solid foundation for further lead optimization facilitated by the structure-based drug design technique.

4-hydroxy-2-quinolone-nitrogen-(4-quinazolinone)-3-formamide derivatives

The invention belongs to the technical field of antibacterial drugs and relates to 4-hydroxy-2-quinolone-nitrogen-(4-quinazolinone)-3-formamide derivatives as well as a preparation method and an application thereof as an antibacterial drug. The compounds are shown in a formula (I), wherein R1 is selected from hydrogen, trifluoromethyl, C1-C8 alkyl, C1-C8 alkoxy and halogen; R2 is selected from hydrogen, nitryl, C1-C8 alkyl, C1-C8 alkoxy and halogen; R3 is selected from C1-C8 alkyl and aryl methyl; R4 is selected from C1-C8 alkyl. The 4-hydroxy-2-quinolone-nitrogen-(4-quinazolinone)-3-formamidederivatives are first discovered antibacterial compounds of novel structures, the compounds have higher inhibition functions on gram-positive bacteria including staphylococcus aureus, staphylococcusepidermidis, enterococcus and the like, particularly, drug-resistant gram-positive bacteria (MRSA (methicillin-resistant staphylococcus aureus), MRSE (methicillin-resistant staphylococcus epidermidis)and VRE (vancomycin-resistant enterococci)) and can be used for following further modification and development.

A novel templates of piperazinyl-1,2-dihydroquinoline-3-carboxylates: Synthesis, anti-microbial evaluation and molecular docking studies

A series of piperazinyl-1,2-dihydroquinoline carboxylates were synthesized by the reaction of ethyl 4-chloro-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylates with various piperazines and their structures were confirmed by 1H NMR, 13C NMR, IR and mass spectral analysis. All the synthesized compounds were screened for their in vitro antimicrobial activities. Further, the in silico molecular docking studies of the active compounds was performed to explore the binding interactions between piperazinyl-1,2-dihydroquinoline carboxylate derivatives and the active site of the Staphylococcus aureus (CrtM) dehydrosqualene synthase (PDB ID: 2ZCQ). The docking studies revealed that the synthesized derivatives showed high binding energies and strong H-bond interactions with the dehydrosqualene synthase validating the observed antimicrobial activity data. Based on antimicrobial activity and docking studies, the compounds 9b and 10c were identified as promising antimicrobial lead molecules. This study might provide insights to identify new drug candidates that target the S. aureus virulence factor, dehydrosqualene synthase.

IMPROVED SOLUBILITY FOR TARGET COMPOUNDS

The present disclosure relates to compounds having an improved solubility thereby increasing their bioavailability, lower dosages, etc. The target compounds, may include but are not limited to, macrophage migration inhibitory factor (MIF) inhibitors, epid

Heterocyclic GSK-3 Allosteric Modulators

The present invention relates to heterocyclic substituted quinoline derivatives as allosteric inhibitors of the glycogen synthase kinase-3 (GSK-3) enzyme. Therefore, these compounds are useful for the manufacturing of a medicament designed for the treatme

HETEROCYCLIC GSK-3 ALLOSTERIC MODULATORS

The invention relates to heterocyclic derivatives of substituted quinolines as allosteric inhibitors of the glycogen synthase kinase 3 (GSK-3) enzyme. Thus, said compounds can be used in the production of a drug for the treatment and/or prevention of diseases in which GSK-3 is involved, such as: neurodegenerative diseases, inflammatory diseases, cancer and diabetes, as well as to promote a plurality of regenerative processes..

4-hydroxy-2-quinolones. 30. Alkylation of 1H-2-oxo-3-carbethoxy-4-hydroxyquinoline

A study has been made of the alkylation of 1H-2-oxo-3-carbethoxy-4-hydroxyquinoline by alkyl halides in the presence of inorganic bases. New methods for the synthesis of 1-substituted 2-oxo-3-carbethoxy-4-hydroxyquinolines are examined. 1997 Plenum Publishing Corporation.