26832-96-2

Usage

Uses

Used in Organic Synthesis:
(4-FLUOROPHENYLAMINO)METHYLENEMALONIC ACID DIETHYL ESTER is used as a building block in organic synthesis for the creation of various biologically active molecules. Its unique structure allows for the development of new compounds with potential applications in various fields.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (4-FLUOROPHENYLAMINO)METHYLENEMALONIC ACID DIETHYL ESTER is used as a key intermediate in the synthesis of pharmaceuticals. Its reactivity and the presence of a fluorine atom attached to the phenyl ring make it a valuable component in the development of new drugs with improved properties.
It is important to handle and use (4-FLUOROPHENYLAMINO)METHYLENEMALONIC ACID DIETHYL ESTER with caution, as it may have potential health and environmental hazards. Proper safety measures should be taken during its synthesis, storage, and application to minimize any risks associated with its use.

InChI:InChI=1/C14H16FNO4/c1-3-19-13(17)12(14(18)20-4-2)9-16-11-7-5-10(15)6-8-11/h5-9,16H,3-4H2,1-2H3

Upstream product

• 40131-09-7 diethyl methoxymethylenemalonate 
• 371-40-4 4-fluoroaniline 
• 105-53-3 diethyl malonate 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 

Downstream Products

• 318-35-4 ethyl 6-fluoro-4-hydroxy-3-quinoline-carboxylate 
• 1435910-85-2 ethyl 6-fluoro-1-(oxiran-2-ylmethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 3832-97-1 1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 873051-19-5 N-(2,4-di-tert-butyl-5-hydroxyphenyl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxamide 
• 1456629-63-2 1-ethyl-6-fluoro-4-oxo-1,4-dihydro-3-[1-oxo-2-hydrazino-3-{p-toluenesulfon}]quinoline 
• 343-10-2 6-fluoro-4-hydroxy-quinoline-3-carboxylic acid 
• 343-10-2 6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 77779-49-8 4-chloro-6-fluoroquinoline-3-carboxylic acid ethyl ester 
• 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 
• 71083-00-6 ethyl 6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate 

Relevant academic research and scientific papers

Bacterial patterning controlled by light exposure

Patterning of multiple bacterial strains in one system is achieved by employing a single photo-activated antibiotic. Varying the light-exposure time results in zones with mixed and single populations.

Design, synthesis, in vitro and in silico studies of novel 4-oxoquinoline ribonucleoside derivatives as HIV-1 reverse transcriptase inhibitors

Human immunodeficiency virus type 1 (HIV-1) is a public health problem that affects over 38 million people worldwide. Although there are highly active antiretroviral therapies, emergence of antiviral resistant strains is a problem which leads to almost a million death annually. Thus, the development of new drugs is necessary. The viral enzyme reverse transcriptase (RT) represents a validated therapeutic target. Because the oxoquinolinic scaffold has substantial biological activities, including antiretroviral, a new series of 4-oxoquinoline ribonucleoside derivatives obtained by molecular hybridization were studied here. All synthesized compounds were tested against human immunodeficiency virus type 1 reverse transcriptase (HIV-1 RT), and 9a and 9d displayed the highest antiviral activities, with IC50 values of 1.4 and 1.6 μM, respectively. These compounds were less cytotoxic than AZT and showed CC50 values of 1486 and 1394 μM, respectively. Molecular docking studies showed that the most active compounds bound to the allosteric site of the enzyme, suggesting a low susceptibility to the development of antiviral resistance. In silico pharmacokinetic and toxicological evaluations reinforced the potential of the active compounds as anti-HIV candidates for further exploration. Overall, this work showed that compounds 9a and 9d are promising scaffold for future anti-HIV-1 RT drug design.

3-(Benzo[: D] thiazol-2-yl)-4-aminoquinoline derivatives as novel scaffold topoisomerase i inhibitor via DNA intercalation: Design, synthesis, and antitumor activities

Twenty-seven 3-(benzo[d]thiazol-2-yl)-4-aminoquinoline derivatives have been designed and synthesized as topoisomerase I inhibitors. The in vitro anti-proliferation evaluation against four human cancer cell lines (MGC-803, HepG-2, T24, and NCI-H460) and one normal cell line (HL-7702) indicated that most of them exhibited potent cytotoxicity. Among them, 5a was identified as the most promising candidate with a low IC50 value of about 2.20 ± 0.14 and was selected for further exploration. Spectroscopic analyses and agarose-gel electrophoresis assays indicated that 5a could interact with DNA and strongly inhibit topoisomerase I (Topo I). Further screening of the Topo I activity of compounds 5b, 5c, 5e, 5f, 5h, 5i, 5j, 5l, and 5n suggested that some of the compounds might exert quite a different cytotoxicity profile to that of 5a. Molecular modeling studies confirmed that 5a adopts a unique mode to interact with DNA and Topo I. Other molecular mechanistic studies suggested that the treatment of MGC-803 cells with 5a induces S phase arrest, up-regulates the pro-apoptotic protein, down-regulates the anti-apoptotic protein, activates caspase-3, and subsequently induces mitochondrial dysfunction so as to induce cell apoptosis. The in vivo efficiency of 5a was also evaluated on MGC-803 xenograft nude mice and the relative tumor growth inhibition was 42.4percent at 12 mg kg-1 without an obvious loss in the body weight. This journal is

6-substituted-1-((1-substituted phenyl-1,2,3-triazole-4-yl)methyl)-4-carbonylquinoline-3-ethyl formate compound, and preparation and application thereof

The invention specifically discloses a 6-substituted-1-((1-substituted phenyl-1,2,3-triazole-4-yl)methyl)-4-carbonylquinoline-3-ethyl formate compound, and preparation and application thereof, belonging to the technical field of organic synthesis. The com

6-substituted-1-((1-substituted phenyl-1,2,3-triazole-4-yl)methyl)-4-carbonylquinoline-3-carboxylic acid or pharmaceutical salt, preparation and application

The present invention belongs to the technical field of organic synthesis, and specifically discloses 6-substituted-1-((1-substituted phenyl-1,2,3-triazole-4-yl)methyl)-4-carbonylquinoline-3-carboxylic compounds or a pharmaceutical salt thereof, and prepa

Compound with carbostyril and beta-lactam structure and synthesis method thereof

The invention provides a compound with a carbostyril and beta-lactam structure and a synthesis method thereof. The molecular structure of the compound is as shown in the specification, and the compound is 6-(1-ethyl-6-fluorin-4-oxo-1,4-dihydro-quinoline-3

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.

Rational design of partial agonists for the muscarinic M1 acetylcholine receptor

Aiming to design partial agonists for a G-protein-coupled receptor based on dynamic ligand binding, we synthesized three different series of bipharmacophoric ligands composed of the orthosteric building blocks iperoxo and 1 linked to allosteric modulators (BQCA-derived compounds, BQCAd; TBPB-derived compound, TBPBd). Their interactions were studied with the human muscarinic acetylcholine M1-receptor (hM1) with respect to receptor binding and Gq-protein signaling. Results demonstrate that iperoxo/BQCAd (2, 3) and 1/BQCAd hybrids (4) act as M1 partial agonists, whereas 1/TBPBd hybrids (5) did not activate M1-receptors. Among the iperoxo/BQCAd-hybrids, spacer length in conjunction with the pattern of substitution tuned efficacy. Most interestingly, a model of dynamic ligand binding revealed that the spacer length of 2a and 3a controlled the probability of switch between the inactive purely allosteric and the active bitopic orthosteric/allosteric binding pose. In summary, dynamic ligand binding can be exploited in M1 receptors to design partial agonists with graded efficacy.

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.