N-(2,5-Dimethoxy-benzyl)-N-(4-fluoro-2-phenoxy-phenyl)-acetamide | 220551-91-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2,5-Dimethoxy-benzyl)-N-(4-fluoro-2-phenoxy-phenyl)-acetamide
• 英文别名: N-[(2,5-dimethoxyphenyl)methyl]-N-(4-fluoro-2-phenoxyphenyl)acetamide
• CAS: 220551-91-7
• 化学式: C₂₃H₂₂FNO₄
• 分子量: 395.43
• InChiKey: ITHCRZUMMLUQBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-Fluoro-2-phenoxy-phenylamine 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-(2,5-Dimethoxy-benzyl)-N-(4-fluoro-2-phenoxy-phenyl)-acetamide
  参考文献：
  名称：

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

  摘要：

  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. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.050

文献信息

• 18F-Labeled Phenoxyphenyl Nu-benzyl Alkanamid Derivatives for Positron Emission Tomography (PET) Imaging of Peripheral Benzodiazepine Receptor
  申请人：Langstrom Bengt

  公开号：US20090142264A1

  公开（公告）日：2009-06-04

  The present invention provides novel 18 F-labeled phenoxyphenyl N-benzyl alkanamid derivative compounds that are suitable for use as an in vivo imaging agent. A pharmaceutical comprising the compound and a kit for the preparation of the pharmaceutical are also provided. Methods of use and use of claims for novel 18 F-labeled phenoxyphenyl N-benzyl alkanamid derivative compounds are provided as well.
• [EN] 18F-LABELED PHENOXYPHENYL N-BENZYL ALKANAMID DERIVATIVES FOR POSITRON EMISSION TOMOGRAPHY (PET) IMAGING OF PERIPHERAL BENZODIAZEPINE RECEPTOR<br/>[FR] DERIVES DE PHENOXYPHENYL N-BENZYL ALCANAMIDE MARQUES AU 18F POUR IMAGERIE PAR TOMOGRAPHIE D'EMISSION DE POSITRONS (PET) DU RECEPTEUR PERIPHERIQUE DE TYPE BENZODIAZEPINE
  申请人：GE HEALTHCARE LTD

  公开号：WO2007074383A1

  公开（公告）日：2007-07-05

  [EN] The present invention provides novel ¹⁸F-labeled phenoxyphenyl N-benzyl alkanamid derivative compounds that are suitable for use as an in vivo imaging agent. A pharmaceutical comprising the compound and a kit for the preparation of the pharmaceutical are also provided. Methods of use and use of claims for novel ¹⁸F-labeled phenoxyphenyl N-benzyl alkanamid derivative compounds are provided as well.
  [FR] La présente invention concerne des composés dérivés innovants du phénoxyphényl N-benzyl alcanamide marqués au ¹⁸F utilisables in vivo en tant qu'agents d'imagerie. L'invention concerne également un produit pharmaceutique comprenant le composé et un kit pour la préparation du produit pharmaceutique, ainsi que des procédés d'utilisation et des revendications d'utilisation relatives aux composés dérivés innovants du phénoxyphényl N-benzyl alcanamide marqués au ¹⁸F.
• Design, synthesis and structure–affinity relationships of aryloxyanilide derivatives as novel peripheral benzodiazepine receptor ligands
  作者：Taketoshi Okubo、Ryoko Yoshikawa、Shigeyuki Chaki、Shigeru Okuyama、Atsuro Nakazato

  DOI：10.1016/j.bmc.2003.10.050

  日期：2004.1

  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. (C) 2003 Elsevier Ltd. All rights reserved.