2-(azetidine-1-carboxamido)-5-(trifluoromethyl)benzoic acid | 848001-33-2

• 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: 2-(azetidine-1-carboxamido)-5-(trifluoromethyl)benzoic acid
• 英文别名: 2-(azetidine-1-carbonylamino)-5-(trifluoromethyl)benzoic acid
• CAS: 848001-33-2
• 化学式: C₁₂H₁₁F₃N₂O₃
• 分子量: 288.226
• InChiKey: VIOZUXSTRMZDTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  、 2-(azetidine-1-carboxamido)-5-(trifluoromethyl)benzoic acid 在 (benzotriazol-1-yloxy)tris-(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 生成 (+/-)N-[2-{[(2-{[(1S*,2R*)-2-({[4-(methylthio)phenyl]sulfonyl}methyl)cyclohexyl]amino}-2-oxoethyl)amino]carbonyl}-4-(trifluoromethyl)phenyl]-1-azetidinecarboxamide
  参考文献：
  名称：

  Novel sulfone-containing di- and trisubstituted cyclohexanes as potent CC chemokine receptor 2 (CCR2) antagonists

  摘要：

  Potent sulfone-containing di- and trisubstituted cyclohexanes were synthesized and evaluated as CC chemokine receptor 2 (CCR2) antagonists. This led to the trisubstituted derivative 54, which exhibited excellent binding (CCR2 IC50 = 1.3 nM) and functional antagonism (calcium flux IC50 = 0.5 nM and chemotaxis IC50 = 0.2 nM). The superiority of the trisubstituted scaffold was rationalized to be the result of a conformational rigidification, which provided insight into the bioactive conformation of this chemotype. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.041
• 作为产物：
  描述：

  4-(tert-butyl)-1-(2-cyclobutylallyl)-2-(hexa-1,5-dien-2-yl)benzene 在 四氢吡咯 、 四(三苯基膦)钯 作用下， 以 乙腈 为溶剂， 生成 2-(azetidine-1-carboxamido)-5-(trifluoromethyl)benzoic acid
  参考文献：
  名称：

  Novel sulfone-containing di- and trisubstituted cyclohexanes as potent CC chemokine receptor 2 (CCR2) antagonists

  摘要：

  Potent sulfone-containing di- and trisubstituted cyclohexanes were synthesized and evaluated as CC chemokine receptor 2 (CCR2) antagonists. This led to the trisubstituted derivative 54, which exhibited excellent binding (CCR2 IC50 = 1.3 nM) and functional antagonism (calcium flux IC50 = 0.5 nM and chemotaxis IC50 = 0.2 nM). The superiority of the trisubstituted scaffold was rationalized to be the result of a conformational rigidification, which provided insight into the bioactive conformation of this chemotype. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.041

文献信息

• Cyclic derivatives as modulators of chemokine receptor activity
  申请人：Carter H. Percy

  公开号：US20050054627A1

  公开（公告）日：2005-03-10

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

  当前申请描述了MCP-1的调节剂，其化学公式为(I):或其药用可接受的盐形式，用于治疗类风湿性关节炎、多发性硬化症、动脉粥样硬化和哮喘。
• Substituted cycloalkylamine derivatives as modulators of chemokine receptor activity
  申请人：Carter H. Percy

  公开号：US20050054626A1

  公开（公告）日：2005-03-10

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

  本申请描述了MCP-1的调节剂，化学式为(I)：或其药用可接受的盐形式，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。
• 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。
• CYCLIC DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：Carter Percy H.

  公开号：US20090124668A1

  公开（公告）日：2009-05-14

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

  本申请描述了 MCP-1 的调节剂，其化学式为 (I) 或其药学上可接受的盐形式，适用于治疗类风湿性关节炎、多发性硬化症、动脉粥样硬化和哮喘。
• LACTAMS OF ALKYLATED ACYCLIC DIAMINE DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：Carter H. Percy

  公开号：US20070197516A1

  公开（公告）日：2007-08-23

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

  本申请描述了MCP-1调节剂的公式（I）或其药学上可接受的盐形式，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。