1-(4-tert-Butyl-phenyl)-3-hydroxy-1H-indole-2-carboxylic acid ethyl ester | 911815-44-6

• 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)-3-hydroxy-1H-indole-2-carboxylic acid ethyl ester
• CAS: 911815-44-6
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: IBGYCOUSRANQMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  51.46
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(4-tert-Butyl-phenyl)-3-hydroxy-1H-indole-2-carboxylic acid ethyl ester 在 sodium hydroxide 、 copper diacetate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 1-(4-tert-Butyl-phenyl)-3-(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：

  二甲基苯基甘氨酸-o-羧酸酯 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 19.0h， 生成 1-(4-tert-Butyl-phenyl)-3-hydroxy-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