N-(5-fluoro-2-phenoxyphenyl)acetamide | 867252-29-7

• 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-(5-fluoro-2-phenoxyphenyl)acetamide
• CAS: 867252-29-7
• 化学式: C₁₄H₁₂FNO₂
• 分子量: 245.253
• InChiKey: HPBYTOFDSULWOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(5-fluoro-2-phenoxyphenyl)acetamide 在 四(三苯基膦)钯 bis(tri-n-butyl)tin 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 99.0h， 生成 N-(5-fluoro-2-phenoxyphenyl)-N-(2-iodo-5-methoxybenzyl)acetamide
  参考文献：
  名称：

  N-(5-Fluoro-2-phenoxyphenyl)-N-(2-[¹³¹I]iodo-5-methoxybenzyl)acetamide:  A Potent Iodinated Radioligand for the Peripheral-type Benzodiazepine Receptor in Brain

  摘要：

  To image the peripheral-type benzodiazepine receptor (PBR) in vivo, we previously developed two positron emission tomography (PET) ligands, N-(2-[C-11],5-dimethoxybenzyl)-N-(5-fluoro-2-phenoxyphenyl)acetamide ([C-11]1a) and its [F-18]fluoroethyl analogue ([F-18]1b), for the investigation of PBR in the living human brain. This time, using 1a as a leading compound, we designed two novel iodinated analogues, N-(5-fluoro-2-phenoxyphenyl)-N-(2-iodo-5-methoxybenzyl)acetamide (3a) and N-(2,5-dimethoxybenzyl)-N-(5-iodo-2-phenoxyphenyl)acetamide (3b) for the PBR imaging. Ligands 3 were synthesized by the iodination of tributystannyl precursors 10. Radiolabeling for 3 with I-131 was carried out by the reaction of 10 with [I-131]NaI using H2O2 as an oxidizing agent. In vitro competition experiments determined that 3a exhibited both high affinity and selectivity for PBR (IC50: 7.8 nM) vs CBR (> 1 mu M). Biodistribution study in mice determined that [I-131]3a had a high radioactivity level (1.69% dose/g) in the brain, and its distribution pattern in the brain was consistent with the known distribution of PBR in rodents. Ex vivo autoradiography of the rat brain gave visual evidence that [I-131]3a was a potent and specific radioligand for PBR.

  DOI：

  10.1021/jm061127n
• 作为产物：
  描述：

  4-fluoro-2-nitro-1-phenoxybenzene 在 platinum(IV) oxide 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-(5-fluoro-2-phenoxyphenyl)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

• Synthesis of [11C]FEDAA1106 as a new PET imaging probe of peripheral benzodiazepine receptor expression
  作者：Min Wang、Mingzhang Gao、Gary D. Hutchins、Qi-Huang Zheng

  DOI：10.1016/j.ejmech.2008.08.001

  日期：2009.6

  promising radioligands for positron emission tomography (PET) imaging of PBR. This study was designed to develop a new radiolabeled analog of [11C]DAA1106 and [18F]FEDAA1106, [11C]FEDAA1106, for PET imaging of PBR expression in brain and cancer. Precursor N-(5-fluoro-2-phenoxyphenyl)-N-(2-(2-fluoroethoxy)-5-hydroxybenzyl)acetamide (9) was synthesized in multiple steps with moderate to high chemical

  周围的苯并二氮杂receptor受体（PBR）与神经炎症和肿瘤进展有关。[ 11 C] DAA1106和[ 18 F] FEDAA1106是用于PBR的正电子发射断层扫描（PET）成像的两种有前途的放射性配体。这项研究旨在开发一种新的放射性标记的[ 11 C] DAA1106和[ 18 F] FEDAA1106，[ 11 C] FEDAA1106的类似物，用于在脑和癌症中对PBR表达进行PET成像。前驱体N-（5-氟-2-苯氧基苯基）-N-（2-（2-氟乙氧基）-5-羟基苄基）乙酰胺（9）分多个步骤合成，化学产率中等至较高。前体9用[ 11 C] CH标记3 OTf，并通过高压液相色谱（HPLC）纯化，以提供目标放射性配体N-（5-氟-2-苯氧基苯基）-N-（2-（2-氟乙氧基）-5- [ 11 C]甲氧基苄基）乙酰胺（ [ 11 C] FEDAA1106，[ 11 C] 10）以60–70％的放射化学收率，基于[
• AGENTS FOR THERAPY EFFICACY MONITORING AND DEEP TISSUE IMAGING
  申请人：Bornhop J. Darryl

  公开号：US20080031823A1

  公开（公告）日：2008-02-07

  Compounds and methods related to NIR molecular imaging, in-vitro and in-vivo functional imaging, therapy/efficacy monitoring, and cancer and metastatic activity imaging. Compounds and methods demonstrated pertain to the field of peripheral benzodiazepine receptor imaging, metabolic imaging, cellular respiration imaging, cellular proliferation imaging as targeted agents that incorporate signaling agents.

  与近红外分子成像、体外和体内功能成像、治疗/疗效监测以及癌症和转移活动成像相关的化合物和方法。展示的化合物和方法涉及外周苯二氮平受体成像、代谢成像、细胞呼吸成像、细胞增殖成像作为包含信号剂的靶向剂。
• Phenyloxyaniline derivatives
  申请人：Lehmann Lutz

  公开号：US20080177108A1

  公开（公告）日：2008-07-24

  The present invention relates to phenyloxyaniline derivatives, to methods of their production and to uses thereof.

  本发明涉及苯氧基苯胺衍生物，其生产方法和用途。
• PHENYLOXYANILINE DERIVATIVES
  申请人：LEHMANN Lutz

  公开号：US20110097269A1

  公开（公告）日：2011-04-28

  The present invention relates to phenyloxyaniline derivatives, to methods of their production and to uses thereof.

  本发明涉及苯氧基苯胺衍生物，其生产方法和用途。
• Agents for therapy efficacy monitoring and deep tissue imaging
  申请人：Vanderbilt University

  公开号：US08188116B2

  公开（公告）日：2012-05-29

  Compounds and methods related to NIR molecular imaging, in-vitro and in-vivo functional imaging, therapy/efficacy monitoring, and cancer and metastatic activity imaging. Compounds and methods demonstrated pertain to the field of peripheral benzodiazepine receptor imaging, metabolic imaging, cellular respiration imaging, cellular proliferation imaging as targeted agents that incorporate signaling agents.

  与近红外分子成像、体外和体内功能成像、治疗/疗效监测以及癌症和转移活性成像相关的化合物和方法。所示化合物和方法涉及外周苯二氮平受体成像、代谢成像、细胞呼吸成像、细胞增殖成像作为包含信号剂的靶向药物。