1-(4-tert-Butyl-phenyl)-6-chloro-3-(4-trifluoromethyl-pyridin-2-yloxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester | 911846-66-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(4-tert-Butyl-phenyl)-6-chloro-3-(4-trifluoromethyl-pyridin-2-yloxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester
• CAS: 911846-66-7
• 化学式: C₂₆H₂₃ClF₃N₃O₃
• 分子量: 517.935
• InChiKey: GIZUMALVEMDWMY-UHFFFAOYSA-N

物化性质

• 沸点：
  536.4±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.36
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.24
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-(4-tert-Butyl-phenyl)-6-chloro-3-(4-trifluoromethyl-pyridin-2-yloxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以90%的产率得到1-(4-tert-Butyl-phenyl)-6-chloro-3-(4-trifluoromethyl-pyridin-2-yloxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological activities of novel aryl indole-2-carboxylic acid analogs as PPARγ partial agonists

  摘要：

  A series of novel aryl indole-2-carboxylic acids has been identified as potent selective PPAR gamma modulators. Their chemical synthesis and in vitro activities are discussed. Compound 5 was selected for in vivo testing in the db/db mouse model of type 2 diabetes and resulted in reduction of hyperglycemia at comparable plasma exposure when compared to rosiglitazone. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.002
• 作为产物：
  描述：

  ethyl (4-(tert-butyl)phenyl)glycinate 在 copper diacetate 、 sodium ethanolate 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-(4-tert-Butyl-phenyl)-6-chloro-3-(4-trifluoromethyl-pyridin-2-yloxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and biological activities of novel aryl indole-2-carboxylic acid analogs as PPARγ partial agonists

  摘要：

  A series of novel aryl indole-2-carboxylic acids has been identified as potent selective PPAR gamma modulators. Their chemical synthesis and in vitro activities are discussed. Compound 5 was selected for in vivo testing in the db/db mouse model of type 2 diabetes and resulted in reduction of hyperglycemia at comparable plasma exposure when compared to rosiglitazone. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.002