19357-07-4

Usage

Uses

Used in Pharmaceutical Synthesis:
2-[(Benzylamino)carbonyl]benzoic acid is used as a key building block in the development of pharmaceuticals, contributing to the creation of new drugs with potential therapeutic benefits.
Used in Agrochemical Production:
In the agrochemical industry, 2-[(Benzylamino)carbonyl]benzoic acid is utilized as a fundamental component in the synthesis of various agrochemicals, enhancing crop protection and yield.
Used in Cancer Research:
2-[(Benzylamino)carbonyl]benzoic acid is studied for its potential as an enzyme inhibitor, specifically targeting enzymes that play a role in the progression of cancer. This application aims to develop new treatments that can help manage and combat cancer.
Used in Antioxidant and Anti-Inflammatory Applications:
Due to its antioxidant and anti-inflammatory properties, 2-[(Benzylamino)carbonyl]benzoic acid is employed in various applications where these characteristics are beneficial, such as in the development of health supplements, skincare products, and other formulations that require these properties to support overall health and well-being.

Upstream product

• 85-44-9 phthalic anhydride 
• 100-46-9 benzylamine 
• 2142-01-0 N-benzylphthalimide 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 136918-14-4 phthalimide 
• 39020-79-6 2-(allyloxy)isoindoline-1,3-dione 
• 524-38-9 N-hydroxyphthalimide 
• 601-70-7 3,3-dichlorophthalide 

Downstream Products

• 2142-01-0 N-benzylphthalimide 
• 1390623-35-4 (S)-1-(2-(benzylcarbamoyl)benzoyl)pyrrolidine-2-carboxamide 
• 1390623-32-1 (S)-N-benzyl-2-(2-cyanopyrrolidine-1-carbonyl)benzamide 
• 38228-99-8 N,N'-dibenzylphthalamide 

Relevant academic research and scientific papers

A phthalimidation protocol that follows protein defined parameters

This work outlines the first phthalimidation protocol suitable for protein labeling and performed in aqueous media at room temperature and neutral pH with no catalyst or co-reagent required. The methodology is suitable for a range of amines and its efficiency was determined with chemoselective and site-selective protein labeling. This journal is

Virtual screening and computational optimization for the discovery of covalent prolyl oligopeptidase inhibitors with activity in human cells

Our docking program, Fitted, implemented in our computational platform, Forecaster, has been modified to carry out automated virtual screening of covalent inhibitors. With this modified version of the program, virtual screening and further docking-based optimization of a selected hit led to the identification of potential covalent reversible inhibitors of prolyl oligopeptidase activity. After visual inspection, a virtual hit molecule together with four analogues were selected for synthesis and made in one-five chemical steps. Biological evaluations on recombinant POP and FAPα enzymes, cell extracts, and living cells demonstrated high potency and selectivity for POP over FAPα and DPPIV. Three compounds even exhibited high nanomolar inhibitory activities in intact living human cells and acceptable metabolic stability. This small set of molecules also demonstrated that covalent binding and/or geometrical constraints to the ligand/protein complex may lead to an increase in bioactivity.

Additive-free chemoselective acylation of amines

Aliphatic and aromatic amines are efficiently acylated by acetic, pivalic, benzoic, phthalic, or maleic anhydrides in ethyl acetate at room temperature. Under the same experimental conditions, amino alcohols are chemoselectively acylated at the amino group.

Solvent effects on alkaline hydrolysis of N-benzylphthalimide in mixed water-acetonitrile and mixed water-N,N-dimethylformamide

The nucleophilic second-order rate constant (kOH) for the reaction of OH- with N-benzylphthalimide appears to follow a reaction mechanism similar to that for reactions of OH- with phthalimide and its N-alkylphthalimides. The rate of hydrolysis reveals an insignificant contribution of water-catalysed cleavage of NBPT compared with its hydroxide ion catalysed reaction. The observed pseudo first-order rate constant, k obs, for alkaline hydrolysis of NBPT decreases with increase in the content of organic cosolvents (up to 70%, v/v) in mixed water-CH3CN and water-DMF solvents.

Rational Design of an Indolebutanoic Acid Derivative as a Novel Aldose Reductase Inhibitor Based on Docking and 3D QSAR Studies of Phenethylamine Derivatives

A series of 45 phenethylamine derivatives were synthesized and evaluated for their inhibitory activity against pig kidney aldose reductase (ALR2, EC 1.1.1.21). Their IC50 values ranged from 400 μM to 24 μM. The binding modes of compounds at the active site of ALR2 were examined using flexible docking. The results indicated that phenethylamine derivatives nicely fit into the active pocket of ALR2 by forming various hydrogen bonding and hydrophobic interactions. 3D-QSAR analysis was also conducted using FlexX-docked alignment of the compounds. The best prediction was obtained by CoMSIA combined with hydrophobic and hydrogen bond donor/acceptor field (q 2 = 0.557, r2 = 0.934). A new derivative, 4-oxo-4-(4-hydroxyindole)butanoic acid, was designed, taking into account the CoMSIA field and the binding mode derived by FlexX docking. This rationally designed compound exhibits an ALR2 inhibition with an IC50 value of 7.4 μM, which compares favorably to that of a well-known ALR2 inhibitor, tolrestat (IC50 = 16 μM) and represents a potency approximately 240-fold higher than that of an original phenethylamine lead compound, YUA001.

The reaction of phthalidylidene dichloride with primary amines. Synthesis and X-ray molecular structure of N-substituted phthalisoimides

An efficient method for the synthesis of N-substituted phthalisoimides, by reaction of phthalidylidene dichloride with primary amines, is described. The reactions with arylamines, arylenediamincs and alkylenediamines lead to the corresponding phthalisoimides or bisphthalisoimides in nearly quantitative yields. However, the reactions with alkylamines are not useful because of the relatively high nucleophilicity of alkylamines. Certain particular behaviours of arylamines, associated with the presence of specific ortho-substituents have been found. The reactions of arylamines bearing an o-hydroxymethyl group provide a convenient method for preparing 2-benzoxazinylbenzoic acids. The X-ray crystallographic structures of N-(2-methoxyphenyl)phthalisoimide 3a and 2-(4H-3.1-benzoxazin-2-yl)benzoic acid 15a have been determined.

Intramolecular Trapping of a Ketenimine Carbene Formed on Flash Vacuum Pyrolysis of 3-Phenylimino-3H-indazole and 3-Phenyliminoisobenzofuran-1-one

Flash vacuum pyrolysis of 3-phenylimino-3H-indazole yielded biphenylene, benzonitrile and, by loss of dinitrogen followed by intramolecular trapping of a ketenimine carbene intermediate, the isomers fluorenimine, phenanthridine and 2-phenylbenzonitrile.Pyrolysis of 3-phenyliminoisobenzofuran-1-one gave the same five products together with N-phenylphthalimide.It is proposed that the same ketenimine carbene intermediate is involved in the two reactions.Pyrolysis of 3-o-tolylimino- and 3-benzylimino-isobenzofuran-1-one led to fragmentation without intramolecular trapping.Pyrolysis of 3-t-butyliminoisobenzofuran-1-one gave o-cyanobenzoic acid.