69066-43-9

Basic information

• Product Name: [(4-fluorophenyl)amino](oxo)acetic acid
• Synonyms: [(4-fluorophenyl)amino](oxo)acetic acid;acetic acid, [(4-fluorophenyl)amino]oxo-;Albb-009509;[(4-fluorophenyl)amino](oxo)acetic acid(SALTDATA: FREE);2-[(4-fluorophenyl)amino]-2-keto-acetic acid;2-[(4-fluorophenyl)amino]-2-oxoacetic acid;2-[(4-fluorophenyl)amino]-2-oxo-acetic acid;2-[(4-fluorophenyl)amino]-2-oxo-ethanoic acid
• CAS NO: 69066-43-9
• Molecular Formula: C₈H₆FNO₃
• Molecular Weight: 183.14
• Mol File: 69066-43-9.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.509g/cm³
• Refractive Index: 1.61
• CAS DataBase Reference: [(4-fluorophenyl)amino](oxo)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [(4-fluorophenyl)amino](oxo)acetic acid(69066-43-9)
• EPA Substance Registry System: [(4-fluorophenyl)amino](oxo)acetic acid(69066-43-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 69066-43-9(Hazardous Substances Data)

Usage

General Description

The chemical compound [(4-fluorophenyl)amino](oxo)acetic acid is a derivative of phenylacetic acid, containing a fluorine atom attached to the phenyl group, an amino group at the para position, and a carboxylic acid functional group. It is also known as 4-fluorophenylglycine and is used primarily as a building block in the synthesis of pharmaceuticals and agrochemicals. [(4-fluorophenyl)amino](oxo)acetic acid is involved in the production of various drugs and is a key intermediate in the pharmaceutical industry. It is also used as a chiral auxiliary in asymmetric synthesis and as a ligand in metal-catalyzed reactions. Additionally, studies have shown its potential in the treatment of various medical conditions, including neurological disorders and cancer.

InChI:InChI=1/C8H6FNO3/c9-5-1-3-6(4-2-5)10-7(11)8(12)13/h1-4H,(H,10,11)(H,12,13)

Upstream product

• 69066-46-2 methyl 2-[(4-fluorophenyl)amino]-2-oxoacetate 
• 69065-91-4 ethyl 2-(4-fluorophenylamino)-2-oxoacetate 
• 371-40-4 4-fluoroaniline 

Downstream Products

• 298216-89-4 C₁₇H₂₄FN₃O₂ 
• 1375736-94-9 N¹-(4-fluorophenyl)-N²-((5-(2-hydroxyethyl)-4-methylthiazol-2-yl)(piperidin-2-yl)methyl)oxalamide hydrochloride 
• 1375736-84-7 N¹-(4-fluorophenyl)-N²-((5-(hydroxymethyl)-4-methylthiazol-2-yl)(piperidin-2-yl)methyl)oxalamide hydrochloride 
• 1354933-56-4 C₁₆H₁₁FN₂O₄ 
• 1266318-51-7 C₈H₅ClFNO₂ 
• 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 

Relevant articles and documents

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.

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.