5349-00-8

Usage

General Description

2-[(3-ethylphenyl)amino]benzoic acid is a chemical compound with the molecular formula C15H15NO2. It is a white to pale yellow solid and is used in the production of pharmaceuticals. It is an important intermediate in the synthesis of various drugs, particularly in the manufacture of non-steroidal anti-inflammatory drugs (NSAIDs). It is also used as a dye intermediate. 2-[(3-ethylphenyl)amino]benzoic acid has been the subject of various studies and research efforts due to its potential pharmacological properties and its role in drug development.

Upstream product

• 587-02-0 m-ethylaniline 
• 118-91-2 ortho-chlorobenzoic acid 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 586-39-0 1-nitro-3-vinyl-benzene 
• 99-61-6 3-nitro-benzaldehyde 
• 88-65-3 2-bromobenzoic-acid 
• 16497-87-3 potassium o-bromobenzoate 

Relevant academic research and scientific papers

Development of LM98, a Small-Molecule TEAD Inhibitor Derived from Flufenamic Acid

The YAP-TEAD transcriptional complex is responsible for the expression of genes that regulate cancer cell growth and proliferation. Dysregulation of the Hippo pathway due to overexpression of TEAD has been reported in a wide range of cancers. Inhibition of TEAD represses the expression of associated genes, demonstrating the value of this transcription factor for the development of novel anti-cancer therapies. We report herein the design, synthesis and biological evaluation of LM98, a flufenamic acid analogue. LM98 shows strong affinity to TEAD, inhibits its autopalmitoylation and reduces the YAP-TEAD transcriptional activity. Binding of LM98 to TEAD was supported by 19F-NMR studies while co-crystallization experiments confirmed that LM98 is anchored within the palmitic acid pocket of TEAD. LM98 reduces the expression of CTGF and Cyr61, inhibits MDA-MB-231 breast cancer cell migration and arrests cell cycling in the S phase during cell division.

Rational design of agonists for bitter taste receptor TAS2R14: from modeling to bench and back

Human bitter taste receptors (TAS2Rs) are a subfamily of 25 G protein-coupled receptors that mediate bitter taste perception. TAS2R14 is the most broadly tuned bitter taste receptor, recognizing a range of chemically diverse agonists with micromolar-range potency. The receptor is expressed in several extra-oral tissues and is suggested to have physiological roles related to innate immune responses, male fertility, and cancer. Higher potency ligands are needed to investigate TAS2R14 function and to modulate it for future clinical applications. Here, a structure-based modeling approach is described for the design of TAS2R14 agonists beginning from flufenamic acid, an approved non-steroidal anti-inflammatory analgesic that activates TAS2R14 at sub-micromolar concentrations. Structure-based molecular modeling was integrated with experimental data to design new TAS2R14 agonists. Subsequent chemical synthesis and in vitro profiling resulted in new TAS2R14 agonists with improved potency compared to the lead. The integrated approach provides a validated and refined structural model of ligand–TAS2R14 interactions and a general framework for structure-based discovery in the absence of closely related experimental structures.

Structure-activity relationships in a series of anti-inflammatory N-arylanthranilic acids

A large series of N-arylanthranilic acids has been prepared. Many of these compounds show high anti-inflammatory activity as measured by the anti-UV-erythema test. From this series have come the clinically useful nonsteroidal anti-inflammatory agents, flufenamic acid (Arlef), mefenamic acid (Ponstel), and the latest and most potent agent, N-(2,6-dichloro-m-tolyl)anthranilic acid (meclofenamic acid, Meclomen = the sodium salt). The structure-activity relationships of this series is discussed and a graphical representation is presented which allows the prediction of activity of new agents.