2-[6-(trifluoromethyl)-1H-benzimidazol-2-yl]acetic acid | 807316-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-[6-(trifluoromethyl)-1H-benzimidazol-2-yl]acetic acid
• CAS: 807316-09-2
• 化学式: C₁₀H₇F₃N₂O₂
• 分子量: 244.173
• InChiKey: VBVQWGRBUMDYQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-3-(4-ethoxyphenyl)-2-(1-((pyridin-3-ylmethyl)amino)ethyl)quinazolin-4(3H)-one 、 2-[6-(trifluoromethyl)-1H-benzimidazol-2-yl]acetic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (R)-N-(1-(3-(4-ethoxyphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)ethyl)-N-(pyridin-3-ylmethyl)-2-(5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)acetamide
  参考文献：
  名称：

  Optimization of a series of quinazolinone-derived antagonists of CXCR3

  摘要：

  The evaluation of the CXCR3 antagonist AMG 487 in clinic trials was complicated due to the formation of an active metabolite. In this Letter, we will discuss the further optimization of the quinazolinone series that led to the discovery of compounds devoid of the formation of the active metabolite that was seen with AMG 487. In addition, these compounds also feature increased potency and good pharmacokinetic properties. We will also discuss the efficacy of the lead compound 34 in a mouse model of cellular recruitment induced by bleomycin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.032
• 作为产物：
  描述：

  ethyl 2-[6-(trifluoromethyl)-1H-benzimidazol-2-yl]acetate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到2-[6-(trifluoromethyl)-1H-benzimidazol-2-yl]acetic acid
  参考文献：
  名称：

  Optimization of a series of quinazolinone-derived antagonists of CXCR3

  摘要：

  The evaluation of the CXCR3 antagonist AMG 487 in clinic trials was complicated due to the formation of an active metabolite. In this Letter, we will discuss the further optimization of the quinazolinone series that led to the discovery of compounds devoid of the formation of the active metabolite that was seen with AMG 487. In addition, these compounds also feature increased potency and good pharmacokinetic properties. We will also discuss the efficacy of the lead compound 34 in a mouse model of cellular recruitment induced by bleomycin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.032

文献信息

• Malonamides and malonamide derivatives as modulators of chemokine receptor activity
  申请人：——

  公开号：US20040235835A1

  公开（公告）日：2004-11-25

  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MCP-1的调节剂，其化学式为(I):1，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。
• MALONAMIDES AND MALONAMIDE DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：Carter Percy

  公开号：US20070213379A1

  公开（公告）日：2007-09-13

  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，其化学式为(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。
• CYCLIC DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：Bristol-Myers Squibb Company

  公开号：EP1620391A2

  公开（公告）日：2006-02-01
• EP1617803A2
  申请人：——

  公开号：EP1617803A2

  公开（公告）日：2006-01-25
• EP1617803A4
  申请人：——

  公开号：EP1617803A4

  公开（公告）日：2007-01-24