ethyl 2-(3-amino-4-methoxyphenyl)-3-(4-nitrophenyl)propanoate | 400648-60-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: ethyl 2-(3-amino-4-methoxyphenyl)-3-(4-nitrophenyl)propanoate
• 英文别名: 2-(3-amino-4-methoxyphenyl)-3-(4-nitrophenyl)propionic acid ethyl ester
• CAS: 400648-60-4
• 化学式: C₁₈H₂₀N₂O₅
• 分子量: 344.367
• InChiKey: DOGKAQIZZQUYNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3-amino-4-methoxyphenyl)-3-(4-nitrophenyl)propanoate 在 palladium on activated charcoal 氢气 、 三乙酰氧基硼氢化钠 、 三乙胺 作用下， 以 甲醇 、 氯仿 、 乙酸乙酯 为溶剂， 生成 3-[4-(3,5-dichloropyridine-4-carbonylamino) phenyl]-2-{3-[(2,2-dimethylpropionyl)isobutylamino]-4-methoxyphenyl}propionic acid ethyl ester
  参考文献：
  名称：

  2,3-Diphenylpropionic acids as potent VLA-4 antagonists

  摘要：

  The discovery and SAR of 2,3-diphenylpropionic acid derivatives as highly potent VLA-4 antagonists are described. One representative compound, 9cc has inhibited intercellular adhesion by a VCAM-1/VLA-4 interaction with an IC50 of 1.7 nM, and has good pharmacokinetics and oral bioavailability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.089
• 作为产物：
  描述：

  (4-Methoxy-3-{[1-phenyl-meth-(E)-ylidene]-amino}-phenyl)-acetic acid ethyl ester 在 盐酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl 2-(3-amino-4-methoxyphenyl)-3-(4-nitrophenyl)propanoate
  参考文献：
  名称：

  2,3-Diphenylpropionic acids as potent VLA-4 antagonists

  摘要：

  The discovery and SAR of 2,3-diphenylpropionic acid derivatives as highly potent VLA-4 antagonists are described. One representative compound, 9cc has inhibited intercellular adhesion by a VCAM-1/VLA-4 interaction with an IC50 of 1.7 nM, and has good pharmacokinetics and oral bioavailability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.089

文献信息

• Solid-phase synthesis of 2,3-diphenylpropionic acid library as VLA-4 antagonists
  作者：Yoichiro Hoshina、Satoru Ikegami、Kyoko Fujimoto、Akihiko Okuyama、Tatsuhiro Harada、Susan James、Peter G. Griffiths、Zemin Wu、Michael Lilly、Andrew M. Bray

  DOI：10.1016/j.tetlet.2005.10.087

  日期：2005.12

  2,3-Diphenylpropionic acid library for VLA-4 antagonist was synthesized on solid-phase. Comparison of the two synthetic routes via an orthogonal generation of two aromatic amino functional groups are discussed. From this work, several compounds were identified as potent VLA-4 antagonists.

  固相合成了VLA-4拮抗剂的2,3-二苯基丙酸文库。讨论了通过两个芳族氨基官能团的正交生成对两种合成路线的比较。通过这项工作，几种化合物被鉴定为有效的VLA-4拮抗剂。
• Electrochemical C–H Amination: Synthesis of Aromatic Primary Amines via <i>N</i>-Arylpyridinium Ions
  作者：Tatsuya Morofuji、Akihiro Shimizu、Jun-ichi Yoshida

  DOI：10.1021/ja402083e

  日期：2013.4.3

  new method for C-H amination of aromatic compounds based on electrochemical oxidation of aromatic compounds in the presence of pyridine followed by the reaction of the resulting N-arylpyridinium ions with an alkylamine. This new transformation serves as a powerful method for synthesizing aromatic primary amines from aromatic compounds without using metal catalysts and harsh chemical reagents. High chemoselectivity

  我们开发了一种新的芳族化合物 CH 胺化方法，该方法基于芳族化合物在吡啶存在下的电化学氧化，然后将所得 N-芳基吡啶鎓离子与烷基胺反应。这种新的转化是一种从芳香族化合物合成芳香族伯胺的有效方法，无需使用金属催化剂和苛刻的化学试剂。本方法的高化学选择性通过带有硝基的芳族化合物的 CH 胺化得到用于合成 VLA-4 拮抗剂的关键中间体来证明。
• 2,3-Diphenylpropionic acid derivatives or their salts, medicines or cell adhesion inhibitors containing the same, and their usage
  申请人：——

  公开号：US20040072878A1

  公开（公告）日：2004-04-15

  A 2,3-diphenylpropionic acid derivatives or the salts represented by general formula (1) below; and pharmaceutical compositions and cell adhesion inhibitors comprising the derivatives or the salts as the active ingredient. In the formula, A, B and C independently represents a hydrogen atom or a monovalent substituent; and X and X′ independently represents a hydrogen atom or a monovalent substituent. 1

  以下是通式（1）所表示的2,3-二苯丙酸衍生物或其盐；以及以该衍生物或盐作为活性成分的药物组合物和细胞黏附抑制剂。在该式中，A、B和C分别表示氢原子或一价取代基；X和X'分别表示氢原子或一价取代基。
• 2,3-DIPHENYLPROPIONIC ACID DERIVATIVES OR THEIR SALTS, MEDICINES OR CELL ADHESION INHIBITORS CONTAINING THE SAME, AND THEIR USAGE
  申请人：Kaken Pharmaceutical Co., Ltd.

  公开号：EP1325903A1

  公开（公告）日：2003-07-09

  A 2,3-diphenylpropionic acid derivatives or the salts represented by general formula (1) below; and pharmaceutical compositions and cell adhesion inhibitors comprising the derivatives or the salts as the active ingredient. In the formula, A, B and C independently represents a hydrogen atom or a monovalent substituent; and X and X' independently represents a hydrogen atom or a monovalent substituent.

  2,3-二苯基丙酸衍生物或以下通式(1)所代表的盐；以及包含这些衍生物或盐作为活性成分的药物组合物和细胞粘附抑制剂。式中，A、B 和 C 分别代表氢原子或一价取代基；X 和 X'分别代表氢原子或一价取代基。
• EP1325903
  申请人：——

  公开号：——

  公开（公告）日：——