318-35-4

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 6-FLUORO-4-HYDROXY-3-QUINOLINECARBOXYLATE is used as an intermediate in the synthesis of pharmaceutical drugs. Its unique structure and functional groups contribute to the development of new drug candidates with improved pharmacological properties.
Used in Agrochemical Industry:
In the agrochemical industry, ETHYL 6-FLUORO-4-HYDROXY-3-QUINOLINECARBOXYLATE serves as a key component in the synthesis of agrochemicals. Its incorporation into these compounds can enhance their effectiveness in pest control and crop protection.
Used in Chemical Industry:
ETHYL 6-FLUORO-4-HYDROXY-3-QUINOLINECARBOXYLATE is utilized as a building block in the preparation of various organic compounds. Its presence in these compounds can impart new properties and functionalities, expanding the scope of chemical research and development.
Used in Fluorine Chemistry Research:
The presence of the fluorine atom in the molecule of ETHYL 6-FLUORO-4-HYDROXY-3-QUINOLINECARBOXYLATE makes it a valuable compound for studying fluorine-containing compounds and their properties. Researchers can use ETHYL 6-FLUORO-4-HYDROXY-3-QUINOLINECARBOXYLATE to explore the unique characteristics of fluorine and its impact on the overall properties of the molecule, contributing to the advancement of fluorine chemistry.

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 academic research and scientific papers

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

Quinolone analogs 13: Synthesis of novel 1,1′-(2-methylenepropane-1,3-diyl)di(4-quinolone-3-carboxylate) and related compounds

The reaction of the 4-hydroxyquinoline-3-carboxylate 6 with pentaerythritol tribromide gave the 1,1′-(2-methylenepropane-1,3-diyl)di(4-quinolone-3-carboxylate) 11, whose reaction with bromine afforded the 1,1′-(2-bromo-2-bromomethylpropane-1,3-diyl)di(4-quinolone-3-carboxylate) 12. Compound 12 was transformed into the (Z)-1,1′-(2-acetoxymethylpropene-1,3-diyl)di(4-quinolone-3-carboxylate) 13 or (E)-1,1′-[2-(imidazol-1-ylmethyl)propene-1,3-diyl]di(4-quinolone-3-carboxylate) 14. Hydrolysis of the dimer (Z)-13 or (E)-14 with potassium hydroxide provided the (E)-1,1′-(2-hydroxymethylpropene-1,3-diyl)di(4-quinolone-3-carboxylic acid) 15 or (Z)-1,1′-[2-(imidazol-1-ylmethyl)propene-1,3-diyl]di(4-quinolone-3-carboxylic acid) 16, respectively. The nuclear Overhauser effect (NOE) spectral data supported that those hydrolysis resulted in the geometrical conversion of (Z)-13 into (E)-15 or (E)-14 into (Z)-16.

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.

Discovery of plasmodium vivax N -myristoyltransferase inhibitors: Screening, synthesis, and structural characterization of their binding mode

N-Myristoyltransferase (NMT) is a prospective drug target against parasitic protozoa. Herein we report the successful discovery of a series of Plasmodium vivax NMT inhibitors by high-throughput screening. A high-resolution crystal structure of the hit com

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.

Design, synthesis, and biological evaluation of novel quinoline derivatives as HIV-1 Tat-TAR interaction inhibitors

Thirty-two quinoline derivatives were designed and synthesized as HIV-1 Tat-TAR interaction inhibitors. All the compounds showed high antiviral activities in inhibiting the formation of SIV-induced syncytium in CEM174 cells. Nine of them with low cytotoxicities were evaluated by Tat dependent HIV-1 LTR-driven CAT gene expression colorimetric enzyme assay in human 293T cells, indicating effective inhibitory activities of blocking the Tat-TAR interaction. Molecular modeling experiments indicated that these compounds may inhibit Tat-TAR interaction by binding to Tat protein instead of TAR RNA.

THERAPEUTIC PYRAZOLOQUINOLINE UREA DERIVATIVES

The invention provides a novel chemical series of formula I, as well as methods of use thereof for binding to the benzodiazepine site of the GABAA receptor and modulating GABAA, and use of the compound of formula I for the treatment

THERAPEUTIC PYRAZOLOQUINOLINE DERIVATIVES

The invention provides a novel chemical series of formula I, as well as methods of use thereof for binding to the benzodiazepine site of the GABAA receptor and modulating GABAA, and use of the compound of formula I for the treatment of GABAA receptor associated disorders. The general structure of formula I is shown below and can exist in tautomeric forms: The invention further provides a method of modulation of one or more GABAA subtypes in an animal comprising administering to the animal an effective amount of a compound of formula (I).

TRIAZOLE COMPOUNDS AS LIPOXYGENASE INHIBITORS

There is provided compounds of formula (I) wherein W is an optionally substituted aryl or heteroaryl group, and pharmaceutically-acceptable salts thereof, which compounds are useful in the treatment of diseases in which inhibition of the activity of a lipoxygenase (e.g. 15- lipoxygenase) is desired and/or required, and particularly in the treatment of inflammation.

Structure-activity relationship of quinoline derivatives as potent and selective α2c-adrenoceptor antagonists

Starting from two acridine compounds identified in a high-throughput screening campaign (1 and 2, Table 1), a series of 4-aminoquinolines was synthesized and tested for their properties on the human α2- adrenoceptor subtypes (α2A, α2B, and α2C). A number of compounds with good antagonist potencies against the α2C-adrenoceptor and excellent subtype selectivities over the other two subtypes were discovered. For example, (R)-{4-[4-(3,4-dimethylpiperazin-1-yl)phenylamino]quinolin-3-yl}methanol 6j had an antagonist potency of 8.5 nM against, and a subtype selectivity of more than 200-fold for, the α2c-adrenoceptor. Investigation of the structure-activity relationship identified a number of structural features, the most critical of which was an absolute need for a substituent in the 3-position of the quinoline ring. The 3-position on the piperazine ring was also found to play an appreciable role, as substitutions in that position exerted a significant and stereospecific beneficial effect on the α2C- adrenoceptor affinity and potency. Replacing the piperazine ring proved difficult, with 1,4-diazepanes representing the only viable alternative.