N-aminoacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline

• 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-aminoacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline
• 英文别名: 2-amino-N-[(2-methoxyphenyl)methyl]-N-(2-phenoxyphenyl)acetamide
• 化学式: C₂₂H₂₂N₂O₃
• 分子量: 362.428
• InChiKey: AFNXGRCVEMPLDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  64.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-chloroacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline 在 platinum(IV) oxide sodium azide 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-aminoacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline
  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

• Aryloxyaniline derivatives
  申请人：Taisho Pharmaceutical Co., Ltd.

  公开号：US06333358B1

  公开（公告）日：2001-12-25

  An aryloxyaniline derivative represented by the formula: wherein Ar1 and Ar2 are each a substituted or unsubstituted phenyl group, pyridyl group or naphthyl group, R1 is a hydrogen atom, an alkyl group, etc., X1 is a hydrogen atom, an alkyl group, etc., y1 is a branched or unbranched alkylene group having 1 to 6 carbon atoms or a single bond; or a pharmaceutically acceptable salt thereof can provide medicines having a high affinity for MDR, and therefore, exhibiting a therapeutic or preventive effect on anxiety, related diseases thereto, depression, etc.

  由以下公式表示的一种芳基氧基苯胺衍生物：其中Ar1和Ar2分别是取代或未取代的苯基、吡啶基或萘基，R1是氢原子、烷基等，X1是氢原子、烷基等，y1是具有1至6个碳原子的分支或非分支烷基基团或单键；或其药学上可接受的盐，可以提供对多药耐药性(MDR)具有高亲和力的药物，因此对焦虑、相关疾病、抑郁等具有治疗或预防作用。
• Heterocycle substituted aryloxyaniline derivatives and their use as MDR ligands
  申请人：Taisho Pharmaceutical Co., Ltd.

  公开号：US06476056B2

  公开（公告）日：2002-11-05

  An aryloxyaniline derivative represented by the formula: wherein Ar1 and Ar2 are the same or different, and are each a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group or a naphthyl group, provided that Ar1 and Ar2 are not both phenyl or both naphthyl and are not phenyl and naphthyl, R1 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted phenyl group or a group of the formula: —NR2(R3) (wherein R2 and R3 are the same or different, and are each a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, X1 is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a phenoxy group, a halogen atom, a trifluoromethyl group, a carbamoyl group or an aminosulfonyl group, Y1 is a branched or unbranched alkylene group having 1 to 6 carbon atoms or a single bond; and pharmaceutically acceptable salts thereof.

  一种芳氧基苯胺衍生物，其化学式如下：其中Ar1和Ar2相同或不同，每个都是取代或未取代的苯基、取代或未取代的吡啶基或萘基，但要求Ar1和Ar2不能同时是苯基或萘基，也不能同时是苯基和萘基；R1是氢原子，具有1至10个碳原子的取代或未取代的烷基、具有1至10个碳原子的烷氧基、取代或未取代的苯基或化学式为- NR2（R3）（其中R2和R3相同或不同，每个都是氢原子或具有1至10个碳原子的烷基），X1是氢原子、具有1至5个碳原子的烷基、具有1至5个碳原子的烷氧基、苯氧基、卤素原子、三氟甲基基团、氨基甲酰基或氨基磺酰基，Y1是具有1至6个碳原子的分支或非分支烷基或单键；以及其药学上可接受的盐。
• ARYLOXYANILINE DERIVATIVES
  申请人：TAISHO PHARMACEUTICAL CO., LTD

  公开号：EP1004573B1

  公开（公告）日：2002-10-30
• US6333358B1
  申请人：——

  公开号：US6333358B1

  公开（公告）日：2001-12-25
• US6476056B2
  申请人：——

  公开号：US6476056B2

  公开（公告）日：2002-11-05