(2S)-3-[[(2,4-dimethylphenyl)methyl]amino]-2-[[[[3-(trifluoromethyl)benzoyl ]amino]acetyl]amino]-propanoic acid | 439148-63-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-3-[[(2,4-dimethylphenyl)methyl]amino]-2-[[[[3-(trifluoromethyl)benzoyl ]amino]acetyl]amino]-propanoic acid
• 英文别名: (S)-3-(2,4-dimethylbenzylamino)-2-(2-(3-(trifluoromethyl)benzamido)acetamido)propanoic acid；(2S)-3-[(2,4-dimethylphenyl)methylamino]-2-[[2-[[3-(trifluoromethyl)benzoyl]amino]acetyl]amino]propanoic acid
• CAS: 439148-63-7
• 化学式: C₂₂H₂₄F₃N₃O₄
• 分子量: 451.445
• InChiKey: IUGZYYHEZQQRHP-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S)-3-[[(2,4-dimethylphenyl)methyl]amino]-2-[[[[3-(trifluoromethyl)benzoyl ]amino]acetyl]amino]-propanoic acid 在 氨 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 为溶剂， 生成 (2S)-3-[[(2,4-dimethylphenyl)methyl]amino]-2-[[[[3-(trifluoromethyl)benzoyl]amino]acetyl]amino]-propanamide
  参考文献：
  名称：

  Capped diaminopropionamide–glycine dipeptides are inhibitors of CC chemokine receptor 2 (CCR2)

  摘要：

  A new series of CCR2 antagonists has been discovered that incorporates intramolecular hydrogen bonding as a strategy for rigidifying the scaffold. The structure-activity relationship was established through initial systematic modification of substitution pattern and chain length, followed by independent optimization of three different substituents (benzylamine, carboxamide, and benzamide). Several of the acyclic compounds display 10-30 nM binding affinity for CCR2. Moreover, these antagonists are able to block both MCP-1-induced Ca2+ flux and monocyte chemotaxis, and are selective for binding to CCR2 over CCR1 and CCR3. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.028
• 作为产物：
  描述：

  methyl (2S)-3-[[(2,4-dimethylphenyl)methyl]amino]-2-[[[[3-(trifluoromethyl)benzoyl]amino]acetyl]amino]-propanoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (2S)-3-[[(2,4-dimethylphenyl)methyl]amino]-2-[[[[3-(trifluoromethyl)benzoyl ]amino]acetyl]amino]-propanoic acid
  参考文献：
  名称：

  Capped diaminopropionamide–glycine dipeptides are inhibitors of CC chemokine receptor 2 (CCR2)

  摘要：

  A new series of CCR2 antagonists has been discovered that incorporates intramolecular hydrogen bonding as a strategy for rigidifying the scaffold. The structure-activity relationship was established through initial systematic modification of substitution pattern and chain length, followed by independent optimization of three different substituents (benzylamine, carboxamide, and benzamide). Several of the acyclic compounds display 10-30 nM binding affinity for CCR2. Moreover, these antagonists are able to block both MCP-1-induced Ca2+ flux and monocyte chemotaxis, and are selective for binding to CCR2 over CCR1 and CCR3. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.028

文献信息

• Diamines as modulators of chemokine receptor activity
  申请人：——

  公开号：US20030060459A1

  公开（公告）日：2003-03-27

  The present application describes modulators of MCP-1 of formula (I): 1 or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma, multiple sclerosis, artherosclerosis, and rheumatoid arthritis.

  本申请描述了公式(I)的MCP-1调节剂或其药用盐形式，用于预防哮喘、多发性硬化症、动脉粥样硬化和类风湿性关节炎。
• US6974836B2
  申请人：——

  公开号：US6974836B2

  公开（公告）日：2005-12-13
• US7449493B2
  申请人：——

  公开号：US7449493B2

  公开（公告）日：2008-11-11