52851-58-8

Basic information

• Product Name: ethyl 1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate
• Synonyms: ethyl 1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate
• CAS NO: 52851-58-8
• Molecular Formula: C₁₆H₁₉NO₄
• Molecular Weight: 289.32636
• Mol File: 52851-58-8.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Room Temperature
• Solubility: Toluene; DCM
• CAS DataBase Reference: ethyl 1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate(52851-58-8)
• EPA Substance Registry System: ethyl 1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate(52851-58-8)

Safety Data

• Hazardous Substances Data: 52851-58-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate is used as an intermediate in the synthesis of 1-Butyl-3-(1,1-dioxido-2H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-2(1H)-quinolinone (B691765). ethyl 1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate is a heterocyclic inhibitor of the RNA-dependent RNA polymerase enzyme, which is transcribed by the Hepatitis C virus. By targeting this enzyme, B691765 can potentially inhibit the replication of the virus, making it a valuable compound in the development of antiviral treatments for Hepatitis C.

Upstream product

• 17781-85-0 ethyl 1-(butylamino)benzene-2-carboxylate 
• 996-82-7 sodium diethylmalonate 
• 105-53-3 diethyl malonate 
• 16512-56-4 N-butylisatoic acid anhydride 
• 6279-86-3 methanetricarboxylic acid triethyl ester 
• 1126-78-9 N-(n-butyl)aniline 

Downstream Products

• 151449-81-9 1-Butyl-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid (2-amino-phenyl)-amide 
• 300716-10-3 1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid anilide 
• 303093-29-0 1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 4-bromoanilide 
• 372083-32-4 1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid hydrazide 
• 300837-51-8 propyl 4-(1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-carboxamido)benzoate 

Relevant articles and documents

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.

Design, synthesis and biological characterization of a new class of osteogenic (1H)-quinolone derivatives

Smoothened (Smo) is the signal transducer of the Hedgehog (Hh) pathway and its stimulation is considered a potential powerful tool in regenerative medicine to treat severe tissue injuries. Starting from GSA-10, a recently reported Hh activator acting on Smo, we have designed and synthesized a new class of quinolone-based compounds. Modification and decoration of three different portions of the original scaffold led to compounds able to induce differentiation of multipotent mesenchymal cells into osteoblasts. The submicromolar activity of several of these new quinolones (0.4–0.9?μM) is comparable to or better than that of SAG and purmorphamine, two reference Smo agonists. Structure-activity relationships allow identification of several molecular determinants important for the activity of these compounds.

4-HYDROXY-2-QUINOLONES. 22. SYNTHESIS AND BIOLOGICAL PROPERTIES OF 1-ALKYL(ARYL)-2-OXO-3-CERBETHOXY-4-HYDROXYQUINOLINES AND THEIR DERIVATIVES

The presently known method for obtaining ethyl esters of 1-alkyl(or aryl)-2-oxo-4-hydroxyquinoline-3-carboxylic acids and their derivatives has been improved.Results are presented from an investigation of the anticoagulant, analgesic, and antiinflammatory activities of the synthesized compounds.

Pharmaceutical preparation and use of 4-hydroxy-2-quinolinone-3-carboxylic acid esters

Disclosed are compounds which are 4-hydroxy-2-quinolinone-3-carboxylic acid esters, e.g., 1-methyl-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester, useful as anti-allergic agents and intermediates for 1-alkyl-4-alkoxy-quinolin-2(1H)-ones, and prepared by reacting an isatoic anhydride with an alkali metal salt of a malonic ester.