220552-11-4

Basic information

• Product Name: Benzoic acid, 2-[[acetyl(2-phenoxyphenyl)amino]methyl]-, methyl ester
• CAS NO: 220552-11-4
• Molecular Formula: C23H21NO4
• Molecular Weight: 375.424
• Mol File: 220552-11-4.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 2-[[acetyl(2-phenoxyphenyl)amino]methyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 2-[[acetyl(2-phenoxyphenyl)amino]methyl]-, methyl ester(220552-11-4)
• EPA Substance Registry System: Benzoic acid, 2-[[acetyl(2-phenoxyphenyl)amino]methyl]-, methyl ester(220552-11-4)

Safety Data

• Hazardous Substances Data: 220552-11-4(Hazardous Substances Data)

Upstream product

• 75-36-5 acetyl chloride 
• 867252-14-0 N-(2-methoxycarbonylbenzyl)-2-phenoxyaniline 
• 4122-56-9 methyl o-formylbenzoate 
• 108-24-7 acetic anhydride 

Downstream Products

• 220552-13-6 N-acetyl-N-(2-carboxybenzyl)-2-phenoxyaniline 

Relevant articles and documents

Synthesis and evaluation in monkey of two sensitive 11C-labeled aryloxyanilide ligands for imaging brain peripheral benzodiazepine receptors in vivo

We sought to develop 11C-labeled ligands for sensitive imaging of brain peripheral benzodiazepine receptors (PBR) in vivo. Two aryloxyanilides with high affinity for PBR were identified and synthesized, namely, N-acetyl-N-(2-methoxycarbonylbenzyl)-2-phenoxyaniline (3, PBR01) and N-(2-methoxybenzyl)-N-(4-phenoxypyridin-3-yl)acetamide (10, PBR28). 3 was hydrolyzed to 4, which was esterified with [11C]iodomethane to provide [11C]3. The O-desmethyl analogue of 10 was converted into [11C]10 with [11C]iodomethane. [11C]3 and [11C]10 were each injected into monkey to assess their brain kinetics with positron emission tomography (PET). After administration of either radioligand there was moderately high brain uptake of radioactivity. Receptor blocking and displacement experiments showed that a high proportion of this radioactivity was bound specifically to PBR. In monkey and rat, 3 and 10 were rapidly metabolized by ester hydrolysis and N-debenzylation, respectively, each to a single polar radiometabolite. [11C]3 and [11C]10 are effective for imaging PBR in monkey brain. [11C]10 especially warrants further evaluation in human subjects.

Design, synthesis and structure-affinity relationships of aryloxyanilide derivatives as novel peripheral benzodiazepine receptor ligands

Since the peripheral benzodiazepine receptor (PBR) has been primarily found as a high-affinity binding site for diazepam in rat kidney, numerous studies of it have been performed. However, the physiological role and functions of PBR have not been fully elucidated. Currently, we presented the pharmacological profile of two high and selective PBR ligands, N-(2,5-dimethoxybenzyl)-N-(4-fluoro-2-phenoxyphenyl)acetamide (7-096, DAA1106) (PBR: IC50=0.28 nM) and N-(4-chloro-2-phenoxyphenyl)-N-(2- isopropoxybenzyl)acetamide (7-099, DAA1097) (PBR: IC50=0.92 nM). The compounds are aryloxyanilide derivatives, and identified with known PBR ligands such as benzodiazepine (1, Ro5-4864), isoquinoline (2, PK11195), imidazopyridine (3, Alpidem), and indole (5, FGIN-1-27) derivatives. The aryloxyanilide derivatives, which have been derived by opening the diazepine ring of 1, are a novel class as PBR ligands and have exhibited high and selective affinity for peripheral benzodiazepine receptors (PBRs). These novel derivatives would be useful for exploring the functions of PBR. In this paper, the design, synthesis and structure-affinity relationships of aryloxyanilide derivatives are described.