69065-91-4

Usage

Uses

Given the limited information available on ETHYL 2-(4-FLUOROANILINO)-2-OXOACETATE, its specific applications are not clearly defined. However, based on its classification as a phenylpyruvic acid derivative, it may potentially be used in the following industries:
Used in Pharmaceutical Industry:
ETHYL 2-(4-FLUOROANILINO)-2-OXOACETATE could be used as an intermediate in the synthesis of pharmaceutical compounds for various therapeutic applications, given its structural features. Its potential use in drug development would require further research to explore its biological activity and safety profile.
Used in Chemical Research:
In the field of chemical research, ETHYL 2-(4-FLUOROANILINO)-2-OXOACETATE may serve as a subject for studying the properties and reactivity of phenylpyruvic acid derivatives, contributing to the understanding of this class of compounds and potentially leading to the discovery of new applications.

InChI:InChI=1/C10H10FNO3/c1-2-15-10(14)9(13)12-8-5-3-7(11)4-6-8/h3-6H,2H2,1H3,(H,12,13)

Upstream product

• 95-92-1 oxalic acid diethyl ester 
• 371-40-4 4-fluoroaniline 
• 4755-77-5 Ethyl oxalyl chloride 
• 762-21-0 acetylenedicarboxylic acid diethyl ester 

Downstream Products

• 896166-18-0 N-(4-fluorophenyl)-N'-(1-phenylcyclopentylmethyl)ethanediamide 
• 1375736-84-7 N¹-(4-fluorophenyl)-N²-((5-(hydroxymethyl)-4-methylthiazol-2-yl)(piperidin-2-yl)methyl)oxalamide hydrochloride 
• 1375736-94-9 N¹-(4-fluorophenyl)-N²-((5-(2-hydroxyethyl)-4-methylthiazol-2-yl)(piperidin-2-yl)methyl)oxalamide hydrochloride 
• 1338471-39-8 (S)-5-(2,6-difluorophenoxy)-3-[(4-fluoro-phenylaminooxalyl)-amino]-4-oxo-pentanoic acid 
• 1338471-30-9 (S)-3-[(4-fluoro-phenylaminooxalyl)-amino]-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid 
• 1338471-27-4 5-fluoro-3-[(4-fluoro-phenylaminooxalyl)-amino]-4-oxo-pentanoic acid 
• 69066-43-9 2-((4-fluorophenyl)amino)-2-oxoacetic acid 
• 69066-19-9 (4-Fluoro-phenylamino)-thioxo-acetic acid ethyl ester 

Relevant academic research and scientific papers

PYRIDONE COMPOUNDS AND METHODS OF USE IN THE MODULATION OF A PROTEIN KINASE

The present disclosure relates generally to compounds and pharmaceutical compositions suitable as modulators of protein kinases, and methods for their use in treating disorders mediated, at least in part by, protein kinases.

Design, synthesis and biological evaluation of 1-Aryl-5-(4-arylpiperazine-1-carbonyl)-1H-tetrazols as novel microtubule destabilizers

A series of 1-aryl-5-(4-arylpiperazine-1-carbonyl)-1H-tetrazols as microtubule destabilizers were designed, synthesised and evaluated for anticancer activity. Based on bioisosterism, we introduced the tetrazole moiety containing the hydrogen-bond acceptors as B-ring of XRP44X analogues. The key intermediates ethyl 1-aryl-1H-tetrazole-5-carboxylates 10 can be simply and efficiently prepared via a microwave-assisted continuous operation process. Among the compounds synthesised, compound 6–31 showed noteworthy potency against SGC-7901, A549 and HeLa cell lines. In mechanism studies, compound 6–31 inhibited tubulin polymerisation and disorganised microtubule in SGC-7901 cells by binding to tubulin. Moreover, compound 6–31 arrested SGC-7901cells in G2/M phase. This study provided a new perspective for development of antitumor agents that target tubulin.

Visible light-mediated photocatalytic oxidative cleavage of activated alkynes: Via hydroamination: A direct approach to oxamates

The direct oxidative cleavage of activated alkynes via hydroamination has been described using organic photocatalyst under visible-light irradiation at room temperature. In this reaction, the single electron oxidation of an in situ formed enamine followed by radical coupling with an oxidant finally delivers the oxamate. The key features of this photocatalytic reaction are the mild reaction conditions, metal-free organic dye as a photocatalyst, and TBHP playing a dual role as O source and for the regeneration of the photocatalyst.

Design, synthesis and evaluation of antiproliferative and antitubulin activities of 5-methyl-4-aryl-3-(4-arylpiperazine-1-carbonyl)-4H-1,2,4-triazoles

A series of novel 5-methyl-4-aryl-3-(4-arylpiperazine-1-carbonyl)-4H-1,2,4-triazoles possessing 1,2,4-triazole as the hydrogen-bond acceptor were designed, synthesized and evaluated for their antiproliferative and tubulin polymerization inhibitory activities. Some of them exhibited moderate activities in vitro against the three cancer cell lines including SGC-7901, A549 and HeLa. Compound 6e exhibited the highest potency against the three cancer cell lines. Moreover, the tubulin polymerization experiments indicated that compound 6e could inhibit the tubulin polymerization. Immunofluorescence study and cell cycle analysis clearly revealed compound 6e could disrupt intracellular microtubule organization, arrest cell cycle at the G2/M phase. In addition, molecular docking analysis demonstrated the interaction of compound 6e at the colchicine-binding site of tubulin. These preliminary results suggested that compound 6e is a new colchicine binding site inhibitor and worthy of further investigation.

Discovery of Cytochrome P450 4F11 Activated Inhibitors of Stearoyl Coenzyme A Desaturase

Stearoyl-CoA desaturase (SCD) catalyzes the first step in the conversion of saturated fatty acids to unsaturated fatty acids. Unsaturated fatty acids are required for membrane integrity and for cell proliferation. For these reasons, inhibitors of SCD represent potential treatments for cancer. However, systemically active SCD inhibitors result in skin toxicity, which presents an obstacle to their development. We recently described a series of oxalic acid diamides that are converted into active SCD inhibitors within a subset of cancers by CYP4F11-mediated metabolism. Herein, we describe the optimization of the oxalic acid diamides and related N-acyl ureas and an analysis of the structure-activity relationships related to metabolic activation and SCD inhibition.

The effect of fluorine atom on the synthesis and composition of gametocidal ethyl oxanilates

Three derivatives of ethyl oxanilate were synthesized in order to test their application as gametocides on the hermaphrodite plants like common wheat (Triticum aestivum L.). A substituent at para position (F, Br, CN) of aniline defined its reactivity towa

Design, synthesis, and antiviral activity of entry inhibitors that target the CD4-binding site of HIV-1

The CD4 binding site on HIV-1 gp120 has been validated as a drug target to prevent HIV-1 entry to cells. Previously, we identified two small molecule inhibitors consisting of a 2,2,6,6-tetramethylpiperidine ring linked by an oxalamide to a p-halide-substituted phenyl group, which target this site, specifically, a cavity termed "Phe43 cavity". Here we use synthetic chemistry, functional assessment, and structure-based analysis to explore variants of each region of these inhibitors for improved antiviral properties. Alterations of the phenyl group and of the oxalamide linker indicated that these regions were close to optimal in the original lead compounds. Design of a series of compounds, where the tetramethylpiperidine ring was replaced with new scaffolds, led to improved antiviral activity. These new scaffolds provide insight into the surface chemistry at the entrance of the cavity and offer additional opportunities by which to optimize further these potential-next- generation therapeutics and microbicides against HIV-1.

Synthesis and biological evaluation of novel oxalamido derivatives as caspase-3 inhibitors

A new series of 5-fluoro-3-[(4-substituted-phenylaminooxalyl)-amino]-4-oxo- pentanoic acid, 7a-c, 3-[(4-substitutedphenylaminooxalyl)- amino]-4-oxo-5-(2,3, 5,6-tetrafluoro-phenoxy)-pentanoic acid, 7d-h and 5-(2,6-difluoro-phenoxy)-3- [(substituted-phenylaminooxalyl)-amino]-4-oxo-pentanoic acid, 7i-p have been synthesized from N-(substituted-phenyl)- oxalamic acid, 1 and their activities have been evaluated in vitro. Compounds 7b,c and k show low micromolar inhibitory activity against caspase-3.

CD4 mimics targeting the mechanism of HIV entry

A structure-activity relationship study was conducted of several CD4 mimicking small molecules which block the interaction between HIV-1 gp120 and CD4. These CD4 mimics induce a conformational change in gp120, exposing its co-receptor-binding site. This induces a highly synergistic interaction in the use in combination with a co-receptor CXCR4 antagonist and reveals a pronounced effect on the dynamic supramolecular mechanism of HIV-1 entry.

Chemical hybridizing agents for chickpea (Cicer arietinum L.): Leads from QSAR analysis of ethyl oxanilates and pyridones

In the self-pollinated crops such as chickpea, induction of male sterility by deployment of chemical hybridizing agents (CHAs) facilitating "two-line" approach holds immense potential in heterosis breeding. A total of 40 test CHAs comprising 20 ethyl oxanilates and 20 pyridones were screened as potential CHAs on chickpea (variety BG 1088) at 500, 800, and 1000 ppm. Three test compounds mostly having either F (4)/Br (5)/CF3 (19) at the para position of the aryl ring from a pool of 20 ethyl oxanilates were identified as the most potent CHAs causing >99% induction of pollen sterility and >90% total flower sterility at 1000-ppm test concentration. Among pyridone derivatives, N-(4-chlorophenyl)-5-carbethoxy-4,6-dimethyl, 1,2-dihydropyrid-2-one (26) was found to be the most active. Quantitative structure activity relationship (QSAR) analysis has revealed a direct involvement of Swain-Lupton field constant, Fp, with the target bioactivity which implied that field rather than resonance effect (R) had a positive effect on the activity. The real guiding principle for selectivity was found out to be the hydrophobic parameter π value. The QSAR models indicated that increased steric bulk at the 4-position on the phenyl ring is associated with enhanced activity. The CHAs appeared to act by mimicking UDP-glucose, the key substrate in the synthesis of callose, or lead to an imbalance in acid-base equilibrium in pollen mother cells resulting in dissolution of callose wall by premature callase secretion.