2-(Pyrrolidinylcarbonyl)amino-5-trifluoromethylbenzoic acid | 445480-27-3

• 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-(Pyrrolidinylcarbonyl)amino-5-trifluoromethylbenzoic acid
• 英文别名: 2-(pyrrolidine-1-carbonylamino)-5-(trifluoromethyl)benzoic acid
• CAS: 445480-27-3
• 化学式: C₁₃H₁₃F₃N₂O₃
• 分子量: 302.253
• InChiKey: IOZAXIQSJZPYDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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-(Pyrrolidinylcarbonyl)amino-5-trifluoromethylbenzoic 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-pyrrolidinecarboxamide
  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-cyclopentylallyl)-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-(Pyrrolidinylcarbonyl)amino-5-trifluoromethylbenzoic 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

• 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：——

  公开号：US20030004151A1

  公开（公告）日：2003-01-02

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

  本申请描述了式(I)的MCP-1调节剂或其药用盐形式，可用于预防类风湿性关节炎、多发性硬化症、动脉粥样硬化和哮喘。
• CYCLIC DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP1343751A2

  公开（公告）日：2003-09-17
• DIAMINES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：Bristol-Myers Squibb Pharma Company

  公开号：EP1351924A2

  公开（公告）日：2003-10-15
• US6706712B2
  申请人：——

  公开号：US6706712B2

  公开（公告）日：2004-03-16