69066-43-9

Usage

Uses

Used in Pharmaceutical Industry:
[(4-fluorophenyl)amino](oxo)acetic acid is used as a building block for the synthesis of various drugs, contributing to the development of new medications with improved therapeutic properties.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
In the field of asymmetric synthesis, [(4-fluorophenyl)amino](oxo)acetic acid is employed as a chiral auxiliary, facilitating the production of enantiomerically pure compounds, which are essential for the pharmaceutical industry to ensure the desired biological activity and minimize potential side effects.
Used as a Ligand in Metal-Catalyzed Reactions:
[(4-fluorophenyl)amino](oxo)acetic acid also serves as a ligand in metal-catalyzed reactions, enhancing the efficiency and selectivity of various chemical transformations, which is crucial for the synthesis of complex molecules and advanced materials.
Used in Medical Research:
Studies have demonstrated the potential of [(4-fluorophenyl)amino](oxo)acetic acid in the treatment of various medical conditions, including neurological disorders and cancer. Its unique structural features and functional groups make it a promising candidate for the development of novel therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, [(4-fluorophenyl)amino](oxo)acetic acid is utilized as a building block for the synthesis of various agrochemicals, such as herbicides, insecticides, and fungicides, contributing to the development of more effective and environmentally friendly products for agricultural applications.

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

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

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 academic research and scientific papers

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.

Oxamyl dipeptide caspase inhibitors developed for the treatment of stroke

Structural modifications were made to a previously described acyl dipeptide caspase inhibitor, leading to the oxamyl dipeptide series. Subsequent SAR studies directed toward the warhead, P2, and P4 regions of this novel peptidomimetic are described herein.