318-35-4

Basic information

• Product Name: ETHYL 6-FLUORO-4-HYDROXY-3-QUINOLINECARBOXYLATE
• Synonyms: 3-QUINOLINECARBOXYLIC ACID, 6-FLUORO-4-HYDROXY-, ETHYL ESTER;6-FLUORO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER;ETHYL 6-FLUORO-4-HYDROXY-3-QUINOLINECARBOXYLATE;ETHYL 6-FLUORO-4-HYDROXYQUINOLINE-3-CARBOXYLATE;BUTTPARK 18\09-69;AURORA 17947;6-Fluoro-4-hydroxy-3-quinolinecarboxylicacidethylester;ethyl 6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate
• CAS NO: 318-35-4
• Molecular Formula: C₁₂H₁₀FNO₃
• Molecular Weight: 235.21
• Product Categories: blocks;Carboxes;FluoroCompounds;Quinolines;Acids and Derivatives;Heterocycles
• Mol File: 318-35-4.mol
• Article Data: 16

Chemical Properties

• Melting Point: 320-323°C
• Boiling Point: 348 °C at 760 mmHg
• Flash Point: 164.2 °C
• Appearance: /
• Density: 1.318 g/cm³
• Vapor Pressure: 5.2E-05mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 2.40±0.50(Predicted)
• CAS DataBase Reference: ETHYL 6-FLUORO-4-HYDROXY-3-QUINOLINECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 6-FLUORO-4-HYDROXY-3-QUINOLINECARBOXYLATE(318-35-4)
• EPA Substance Registry System: ETHYL 6-FLUORO-4-HYDROXY-3-QUINOLINECARBOXYLATE(318-35-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 318-35-4(Hazardous Substances Data)

Usage

General Description

ETHYL 6-FLUORO-4-HYDROXY-3-QUINOLINECARBOXYLATE is a chemical compound with the molecular formula C13H10FNO4. It is a fluorinated quinoline derivative, which has a hydroxy group and an ester functional group. ETHYL 6-FLUORO-4-HYDROXY-3-QUINOLINECARBOXYLATE is used in the synthesis of pharmaceutical drugs and agrochemicals. It is also used as a building block in the preparation of various organic compounds. The presence of the fluorine atom in the molecule makes it useful for studying fluorine-containing compounds and their properties. ETHYL 6-FLUORO-4-HYDROXY-3-QUINOLINECARBOXYLATE has potential applications in the pharmaceutical, agrochemical, and chemical industries.

InChI:InChI=1/C12H10FNO3/c1-2-17-12(16)9-6-14-10-4-3-7(13)5-8(10)11(9)15/h3-6H,2H2,1H3,(H,14,15)

Upstream product

• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 371-40-4 4-fluoroaniline 
• 26832-96-2 diethyl 2-(4-fluoroanilino)methylenemalonate 
• 101-84-8 diphenylether 

Downstream Products

• 343-10-2 6-fluoro-4-hydroxy-quinoline-3-carboxylic acid 
• 77779-49-8 4-chloro-6-fluoroquinoline-3-carboxylic acid ethyl ester 
• 391-77-5 4-Chloro-6-fluoroquinoline 
• 391-78-6 6-Fluoro-4-hydroxyquinoline 
• 915723-07-8 (R)-4-[4-(3,4-dimethylpiperazin-1-yl)phenylamino]-6-fluoroquinoline-3-carboxylic acid ethyl ester 
• 923585-84-6 6-fluoro-4-[4-(3,3,4-trimethylpiperazin-1-yl)phenylamino]quinoline-3-carboxylic acid ethyl ester 
• 923585-83-5 4-[4-(3,4-dimethylpiperazin-1-yl)phenylamino]-6-fluoroquinoline-3-carboxylic acid ethyl ester 

Relevant articles and documents

Quinolone analogues 10: Synthesis of antimalarial quinolones having pyridyl moiety in N1-side chain

Novel 4-quinolone-3-carboxylates 6,7 and 4-quinolone-3-carboxylic acids 8-11 were synthesized from 4-hydroxyquinoline-3-carboxylates. Ethyl 1-[1-ethoxycarbonyl-2-(4-pyridyl)vinyl]-6-fluoro-4-oxoquinoline-3-carboxylate 7a was found to show antimalarial act

4-Aminoquinoline derivatives as novel Mycobacterium tuberculosis GyrB inhibitors: Structural optimization, synthesis and biological evaluation

Mycobacterial DNA gyrase B subunit has been identified to be one of the potentially underexploited drug targets in the field of antitubercular drug discovery. In the present study, we employed structural optimization of the reported GyrB inhibitor resulting in synthesis of a series of 46 novel quinoline derivatives. The compounds were evaluated for their in vitro Mycobacterium smegmatis GyrB inhibitory ability and Mycobacterium tuberculosis DNA supercoiling inhibitory activity. The antitubercular activity of these compounds was tested over Mtb H37Rv strain and their safety profile was checked against mouse macrophage RAW 264.7 cell line. Among all, three compounds (23, 28, and 53) emerged to be active displaying IC50 values below 1 μM against Msm GyrB and were found to be non-cytotoxic at 50 μM concentration. Compound 53 was identified to be potent GyrB inhibitor with 0.86 ± 0.16 μM and an MIC (minimum inhibitory concentration) of 3.3 μM. The binding affinity of this compound towards GyrB protein was analysed by differential scanning fluorimetry which resulted in a positive shift of 3.3 °C in melting temperature (Tm) when compared to the native protein thereby reacertaining the stabilization effect of the compound over protein.

Design and synthesis of some new quinoline-3-carbohydrazone derivatives as potential antimycobacterial agents

A series of 26 new quinoline derivatives carrying active pharmacophores has been synthesized and evaluated for their in vitro antituberculosis activity against Mycobacterium tuberculosis H37Rv (MTB), Mycobacterium smegmatis (MC2), and Mycobacterium fortuitum following the broth micro dilution assay method. Compounds 13e, 13i, 13k, 14a, 14c, 14i, and 14k exhibited significant minimum inhibition concentrations, when compared with first line drugs isoniazid (INH) and rifampicin (RIF) and could be ideally suited for further modifications to obtain more efficacious compounds in the fight against multi-drug resistant tuberculosis.