3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)-1H-indol-1-yl]methyl]phenol | 1139688-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)-1H-indol-1-yl]methyl]phenol
• 英文别名: 3-{[3-(4-Chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)-1H-indol-1-YL]methylphenol；(4-chlorophenyl)-[1-[(3-hydroxyphenyl)methyl]-2-methyl-6-(trifluoromethoxy)indol-3-yl]methanone
• CAS: 1139688-46-2
• 化学式: C₂₄H₁₇ClF₃NO₃
• 分子量: 459.852
• InChiKey: ULDGCXZYGSLENK-UHFFFAOYSA-N

物化性质

• 沸点：
  581.9±50.0 °C(predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙基1-溴环丁烷甲酸酯 、 3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)-1H-indol-1-yl]methyl]phenol 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Ethyl 1-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]cyclobutane-1-carboxylate
  参考文献：
  名称：

  Discovery of a Peroxisome Proliferator Activated Receptor γ (PPARγ) Modulator with Balanced PPARα Activity for the Treatment of Type 2 Diabetes and Dyslipidemia

  摘要：

  A series of 3-acylindole-1-benzylcarboxylic acids were designed and synthesized while searching for a PPAR gamma modulator with additional moderate intrinsic PPAR alpha agonistic activity. 2-[3-[[3-(4-Chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)-1H-indol-1-yl]methyl]phenoxy]-(2R)-butanoic acid (12d) was identified as such an agent which demonstrated potent efficacy in lowering both glucose and lipids in multiple animal models with significantly attenuated side effects such as fluid retention and heart weight gain associated with PPAR gamma full agonists, The moderate PPAR alpha activity of 12d not only contributed to the agent's ability to manage lipid profiles but also appears to have potentiated its PPAR gamma efficacy in lowering glucose levels in preclinical diabetic animal models.

  DOI：

  10.1021/jm900367w
• 作为产物：
  描述：

  3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)-1H-indol-1-yl]methyl]anisole 在 三溴化硼 、 水 、 碳酸氢钠 、 sodium chloride 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)-1H-indol-1-yl]methyl]phenol
  参考文献：
  名称：

  Discovery of a Peroxisome Proliferator Activated Receptor γ (PPARγ) Modulator with Balanced PPARα Activity for the Treatment of Type 2 Diabetes and Dyslipidemia

  摘要：

  A series of 3-acylindole-1-benzylcarboxylic acids were designed and synthesized while searching for a PPAR gamma modulator with additional moderate intrinsic PPAR alpha agonistic activity. 2-[3-[[3-(4-Chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)-1H-indol-1-yl]methyl]phenoxy]-(2R)-butanoic acid (12d) was identified as such an agent which demonstrated potent efficacy in lowering both glucose and lipids in multiple animal models with significantly attenuated side effects such as fluid retention and heart weight gain associated with PPAR gamma full agonists, The moderate PPAR alpha activity of 12d not only contributed to the agent's ability to manage lipid profiles but also appears to have potentiated its PPAR gamma efficacy in lowering glucose levels in preclinical diabetic animal models.

  DOI：

  10.1021/jm900367w

文献信息

• Discovery of a Peroxisome Proliferator Activated Receptor γ (PPARγ) Modulator with Balanced PPARα Activity for the Treatment of Type 2 Diabetes and Dyslipidemia
  作者：Weiguo Liu、Kun Liu、Harold B. Wood、Margaret E. McCann、Thomas W. Doebber、Ching H. Chang、Taro E. Akiyama、Monica Einstein、Joel P. Berger、Peter T. Meinke

  DOI：10.1021/jm900367w

  日期：2009.7.23

  A series of 3-acylindole-1-benzylcarboxylic acids were designed and synthesized while searching for a PPAR gamma modulator with additional moderate intrinsic PPAR alpha agonistic activity. 2-[3-[[3-(4-Chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)-1H-indol-1-yl]methyl]phenoxy]-(2R)-butanoic acid (12d) was identified as such an agent which demonstrated potent efficacy in lowering both glucose and lipids in multiple animal models with significantly attenuated side effects such as fluid retention and heart weight gain associated with PPAR gamma full agonists, The moderate PPAR alpha activity of 12d not only contributed to the agent's ability to manage lipid profiles but also appears to have potentiated its PPAR gamma efficacy in lowering glucose levels in preclinical diabetic animal models.