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Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 4-CHLORO-6-FLUOROQUINOLINE-3-CARBOXYLATE is used as an active pharmaceutical ingredient for the synthesis of drugs with antibiotic and anti-inflammatory properties. Its unique structure and the presence of chlorine and fluorine atoms enhance its biological activity, making it a promising candidate for the development of new therapeutic agents.
Used in Research and Development:
In the field of research, ETHYL 4-CHLORO-6-FLUOROQUINOLINE-3-CARBOXYLATE is utilized for the development of novel therapeutic agents. Its potential antibiotic and anti-inflammatory properties, along with its unique structure, make it an attractive compound for exploring new treatment options for various infections and inflammatory conditions.
Used in Drug Synthesis:
ETHYL 4-CHLORO-6-FLUOROQUINOLINE-3-CARBOXYLATE is used as a key intermediate in the synthesis of various pharmaceutical drugs. Its presence in the molecular structure of these drugs contributes to their effectiveness in treating infections and inflammatory conditions.
Used in Medicinal Chemistry:
In medicinal chemistry, ETHYL 4-CHLORO-6-FLUOROQUINOLINE-3-CARBOXYLATE is employed as a building block for the design and synthesis of new chemical entities with improved pharmacological properties. Its unique structure and functional groups provide a foundation for the development of innovative drug candidates with enhanced efficacy and safety profiles.
Used in Drug Discovery:
ETHYL 4-CHLORO-6-FLUOROQUINOLINE-3-CARBOXYLATE is utilized in drug discovery processes to identify new lead compounds with potential therapeutic applications. Its antibiotic and anti-inflammatory properties, along with its unique structural features, make it a valuable tool in the search for novel treatments for various diseases and conditions.

InChI:InChI=1/C12H9ClFNO2/c1-2-17-12(16)9-6-15-10-4-3-7(14)5-8(10)11(9)13/h3-6H,2H2,1H3

Upstream product

• 318-35-4 ethyl 6-fluoro-4-hydroxy-3-quinoline-carboxylate 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 18856-68-3 diethyl N,N-dimethylaminomethylenemalonate 
• 71083-00-6 ethyl 6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 371-40-4 4-fluoroaniline 
• 26832-96-2 diethyl 2-(4-fluoroanilino)methylenemalonate 

Downstream Products

• 1215325-47-5 ethyl 4-((R)-1-(dimethylcarbamoyl)-3-(phenylthio)propan-2-ylamino)-6-fluoro quinoline-3-carboxylate 
• 1438234-19-5 (E)-ethyl 4-([1,1'-biphenyl]-4-ylimino)-6-fluoro-1-methyl-1,4-dihydroquinoline-3-carboxylate 
• 1438234-23-1 (E)-ethyl 4-([1,1'-biphenyl]-4-ylimino)-1-ethyl-6-fluoro-1,4-dihydroquinoline-3-carboxylate 

Relevant academic research and scientific papers

Synthesis and screening of triazolopyrimidine scaffold as multi-functional agents for Alzheimer's disease therapies

In present study a series of triazolopyrimidine-quinoline and cyanopyridine-quinoline hybrids were designed, synthesized and evaluated as acetylcholinesterase inhibitors (AChEIs). Molecular docking and scoring was utilized for the design of inhibitors. The molecules were synthesized via an easily accessible, convergent synthetic route. Three triazolopyrimidine based compounds showed nanomolar activity towards acetylcholinesterase. Among them, Ethyl 6-fluoro-4-(4-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)piperazin-1-yl)quinoline-3-carboxylate (10d), strongly inhibited AChE with IC50 value of 42 nM. Furthermore compound 10d was identified as most promising compound with 12 fold selectivity against butyrylcholinesterase (BuChE). This compound displayed a composed multitargeted profile with promising inhibition of self-induced and AChE - induced Aβ aggregation and antioxidant activity.

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.

Quinolin-4(1 H)-imines are potent antiplasmodial drugs targeting the liver stage of malaria

We present a novel series of quinolin-4(1H)-imines as dual-stage antiplasmodials, several-fold more active than primaquine in vitro against Plasmodium berghei liver stage. Among those, compounds 5g and 5k presented low nanomolar IC50 values. The compounds are metabolically stable and modulate several drug targets. These results emphasize the value of quinolin-4(1H)-imines as a new chemotype and their suitable properties for further drug development.

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

Synthesis and anticancer activities of some novel 2-(benzo[d]thiazol-2-yl)- 8-substituted-2H-pyrazolo[4,3-c]quinolin-3(5H)-ones

A series of 2-(benzo[d]thiazol-2-yl)-8-substituted-2H-pyrazolo[4,3-c] quinolin-3(5H)-ones (3a-g) have been synthesized and evaluated for their in vitro antiproliferative activities against four human cancer cell lines: MDA-MB-435 (breast), HL-60 (leukemia), HCT-8 (colon) and SF-295 (central nervous system). The results showed that the compounds 3b (2-(benzo[d]thiazol-2-yl)-8- methyl-2H-pyrazolo[4,3-c]quinolin-3(5H)-one) and 3c (2-(benzo[d]thiazol-2-yl)-8- bromo-2H-pyrazolo[4,3-c]quinolin-3(5H)-one) exhibited good cytotoxicity for three cell lines with IC50 values lower than 5 μg/mL. Analysis of theoretical toxicity risks have shown medium tumorigenic and irritant risks related to 3b and 3c in contrast to doxorubicin, the positive control.

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.

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.