1-(4-tert-Butyl-phenyl)-5-chloro-3-(4-chloro-3-trifluoromethyl-phenoxy)-1H-indole-2-carboxylic acid ethyl ester | 911829-14-6

• 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)-5-chloro-3-(4-chloro-3-trifluoromethyl-phenoxy)-1H-indole-2-carboxylic acid ethyl ester
• CAS: 911829-14-6
• 化学式: C₂₈H₂₄Cl₂F₃NO₃
• 分子量: 550.405
• InChiKey: DNNITQFQHNLOFR-UHFFFAOYSA-N

物化性质

• 沸点：
  539.1±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.22
• 重原子数：
  37.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(4-tert-Butyl-phenyl)-5-chloro-3-(4-chloro-3-trifluoromethyl-phenoxy)-1H-indole-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)-5-chloro-3-(4-chloro-3-trifluoromethyl-phenoxy)-1H-indole-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：

  5-Chlor-2-methoxycarbonylmethylamino-benzoesaeuremethylester 在 copper diacetate 、 三溴化硼 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 35.0h， 生成 1-(4-tert-Butyl-phenyl)-5-chloro-3-(4-chloro-3-trifluoromethyl-phenoxy)-1H-indole-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