117685-48-0

Basic information

• Product Name: 6-FLUORO-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID
• Synonyms: OTAVA-BB BB7018670072;6-FLUORO-4-QUINOLONE-3-CARBOXYLIC ACID;6-FLUORO-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID;6-FLUORO-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID;6-FLUORO-1,4-DIHYDRO-4-OXO-3-QUINOLINECARBOXYLIC ACID;ASISCHEM D48883;1,4-Dihydro-6-fluoro-4-oxoquinoline-3-carboxylic acid;3-Carboxy-1,4-dihydro-6-fluoro-4-oxoquinoline
• CAS NO: 117685-48-0
• Molecular Formula: C10H6FNO3
• Molecular Weight: 207.16
• Mol File: 117685-48-0.mol

Chemical Properties

• Melting Point: 298-300°C
• Boiling Point: 362.7 °C at 760 mmHg
• Flash Point: 173.2 °C
• Appearance: /
• Density: 1.517
• Vapor Pressure: 6.77E-06mmHg at 25°C
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Aqueous Base (Slightly, Sonicated), DMSO (Slightly, Heated, Sonicated)
• PKA: 0.30±0.20(Predicted)
• CAS DataBase Reference: 6-FLUORO-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-FLUORO-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID(117685-48-0)
• EPA Substance Registry System: 6-FLUORO-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID(117685-48-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 117685-48-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid is used as a synthetic intermediate for the production of various pharmaceutical drugs, primarily antibacterial agents. Its unique structure and reactivity make it a promising building block for the synthesis of diverse organic compounds with potential therapeutic applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 6-Fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid is utilized for the development of new drug candidates. Its quinoline ring structure and functional groups provide a versatile platform for the design and synthesis of novel compounds with potential therapeutic properties.
Used in Drug Synthesis:
6-Fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid is employed as a key component in the synthesis of various pharmaceutical drugs. Its reactivity and functionality allow for the formation of a wide range of chemical derivatives, which can be further optimized for improved pharmacological properties, such as enhanced potency, selectivity, and bioavailability.
Used in Antimicrobial Agents:
As a member of the quinolone carboxylic acid class, 6-Fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid is used in the development of antimicrobial agents. Its ability to inhibit bacterial DNA synthesis and disrupt essential cellular processes makes it a valuable asset in the fight against drug-resistant infections.
Used in Drug Discovery:
6-Fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid serves as a starting point for drug discovery efforts. Its unique structural features and potential for chemical modification make it an attractive candidate for the identification of new bioactive compounds with therapeutic potential.

InChI:InChI=1/C10H6FNO3/c11-5-1-2-8-6(3-5)9(13)7(4-12-8)10(14)15/h1-4H,(H,12,13)(H,14,15)/p-1

Upstream product

• 144216-13-7 6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methyl ester 
• 71083-00-6 ethyl 6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 26832-96-2 diethyl 2-(4-fluoroanilino)methylenemalonate 
• 251986-57-9 4,5-dimethoxycarbonyl-1-(4'-fluorophenyl)-1H-pyrrole-2,3-dione 
• 371-40-4 4-fluoroaniline 
• 251986-69-3 6-fluoro-4-oxo-1,4-dihydro-quinoline-2,3-dicarboxylic acid 3-methyl ester 
• 251986-63-7 dimethyl 6-fluoro-4-oxo-1,4-dihydroquinoline-2,3-dicarboxylate 
• 251986-49-9 methyl 3-carbomethoxy-3-(4'-fluorophenyl)amino-2-propenoate 

Downstream Products

• 873051-19-5 N-(2,4-di-tert-butyl-5-hydroxyphenyl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxamide 

Relevant articles and documents

Polysubstituted quinolone compounds, and preparation method and use thereof

The invention provides polysubstituted quinolone compounds, and a preparation method and a use thereof, and concretely provides a polysubstituted quinolone compound represented by formula I, and optical isomers, pharmaceutically acceptable salts or solvates thereof. All groups in the formula I are defined in the description. The quinolone compound has excellent c-Met inhibition activity, and can be used for treating c-Met activity or expression level corrected diseases.

Synthesis and biological evaluation of 4-oxoquinoline-3-carboxamides derivatives as potent anti-fibrosis agents

Thirty-one 4-oxoquinoline-3-carboxamides derivatives were synthesized and evaluated for their anti-fibrotic activities by the inhibition of TGF-β1-induced total collagen accumulation and anti-inflammatory activities by the inhibition of LPS-stimulated TNF-α production. Among them, three compounds (10a, 10l and 11g) exhibited potent inhibitory effects on both TGF-β1-induced total collagen accumulation and LPS-stimulated TNF-α production. Furthermore, oral administrations of 10l at a dose of 20 mg/kg/day for 4 weeks effectively alleviated lung inflammation and injury, and decreased lung collagen accumulation in bleomycin-induced pulmonary fibrosis model. Histopathological evaluation of lung tissue confirmed 10l as a potential, orally active agent for the treatment of pulmonary fibrosis.

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.

A synthesis of 4-quinolone-3-carboxylic acids via pyrolysis of N- aryldioxopyrrolines

A synthesis of 4-quinolone-3-carboxylic acids (8) was achieved by pyrolysis of 4,5-dimethoxycarbonyl-1-aryl-1H-pyrrole-2,3-diones (3) followed by selective demethoxycarbonylation of the resulting 2,3-dimethoxycarbonyl-4- quinolones (4) in excellent overall yields.