4046-39-3

Basic information

• Product Name: 2-[[4-[(2-carboxyphenyl)amino]-3,6-dioxo-1-cyclohexa-1,4-dienyl]amino]benzoic acid
• CAS NO: 4046-39-3
• Molecular Formula: C₂₀H₁₄N₂O₆
• Molecular Weight: 378.341
• Mol File: 4046-39-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-[[4-[(2-carboxyphenyl)amino]-3,6-dioxo-1-cyclohexa-1,4-dienyl]amino]benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[[4-[(2-carboxyphenyl)amino]-3,6-dioxo-1-cyclohexa-1,4-dienyl]amino]benzoic acid(4046-39-3)
• EPA Substance Registry System: 2-[[4-[(2-carboxyphenyl)amino]-3,6-dioxo-1-cyclohexa-1,4-dienyl]amino]benzoic acid(4046-39-3)

Safety Data

• Hazardous Substances Data: 4046-39-3(Hazardous Substances Data)

Usage

Structure

Contains a cyclohexadienyl group and a benzoic acid group

Type

Amino acid derivative

Functional groups

Two amino groups and a carboxylic acid group

Application

Used in pharmaceutical research and development as a potential drug candidate

Significance

Subject of interest for further study and potential therapeutic applications

Upstream product

• 64-17-5 ethanol 
• 118-92-3 anthranilic acid 
• 106-51-4 p-benzoquinone 
• 490-79-9 2,5-dihydroxybenzoic acid. 

Downstream Products

• 1503-48-6 6,7,13,14-tetraoxo-5,6,7,12,13,14-hexahydro-quino{2.3-b}acridine 

Relevant articles and documents

Development of quinone analogues as dynamin GTPase inhibitors

Virtual screening of the ChemDiversity and ChemBridge compound databases against dynamin I (dynI) GTPase activity identified 2,5-bis-(benzylamino)-1,4- benzoquinone 1 as a 273 ± 106 μM inhibitor. In silico lead optimization and focused library-led synthesis resulted in the development of four discrete benzoquinone/naphthoquinone based compound libraries comprising 54 compounds in total. Sixteen analogues were more potent than lead 1, with 2,5-bis-(4-hydroxyanilino)-1,4-benzoquinone (45) and 2,5-bis(4-carboxyanilino)- 1,4-benzoquinone (49) the most active with IC50 values of 11.1 ± 3.6 and 10.6 ± 1.6 μM respectively. Molecular modelling suggested a number of hydrogen bonding and hydrophobic interactions were involved in stabilization of 49 within the dynI GTP binding site. Six of the most active inhibitors were evaluated for potential inhibition of clathrin-mediated endocytosis (CME). Quinone 45 was the most effective CME inhibitor with an IC50(CME) of 36 ± 16 μM.

Structural studies of solid and solution phase reaction products between p-benzoquinone and 2-aminobenzoic acid

Solid and solution phase reaction products between p-benzoquinone and 2-aminobenzoic acids have been characterized using XRD, EPR, NMR and electronic spectra. The solid state reaction product is assigned as 1:1 addition complex while the solution phase re