| 1380695-78-2

• 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
• CAS: 1380695-78-2
• 化学式: C₂₀H₁₈F₃NO₄
• 分子量: 393.362
• InChiKey: SVCSZBMNYUCXPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.55
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 水 、 三溴化硼 、 lithium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (3-(4-trifluoromethyl)phenyl)-5,6-dihydroxy-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and Agonistic Activity at the GPR35 of 5,6-Dihydroxyindole-2-carboxylic Acid Analogues

  摘要：

  5,6-Dihydroxyindole-2-carboxylic acid (DHICA), an intermediate of melanin synthesis and an eumelanin building block, was recently discovered to be a GPR35 agonist with moderate potency. Here, we report the synthesis and pharmacological characterization of a series of DHICA analogues against GPR35 using both label-free, dynamic mass redistribution and Tango beta-arrestin translocation assays. This led to identification of novel GPR35 agonists with improved potency and/or having biased agonism.

  DOI：

  10.1021/ml300076u
• 作为产物：
  描述：

  6-溴藜芦醛 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 sodium carbonate 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Agonistic Activity at the GPR35 of 5,6-Dihydroxyindole-2-carboxylic Acid Analogues

  摘要：

  5,6-Dihydroxyindole-2-carboxylic acid (DHICA), an intermediate of melanin synthesis and an eumelanin building block, was recently discovered to be a GPR35 agonist with moderate potency. Here, we report the synthesis and pharmacological characterization of a series of DHICA analogues against GPR35 using both label-free, dynamic mass redistribution and Tango beta-arrestin translocation assays. This led to identification of novel GPR35 agonists with improved potency and/or having biased agonism.

  DOI：

  10.1021/ml300076u

文献信息

• Expedient synthesis of eumelanin-inspired 5,6-dihydroxyindole-2-carboxylate ethyl ester derivatives
  作者：Andrew H. Aebly、Jeffrey N. Levy、Benjamin J. Steger、Jonathan C. Quirke、Jason M. Belitsky

  DOI：10.1039/c8ra06148c

  日期：——

  Dihydroxyindoles such as 5,6-dihydroxyindole-2-carboxylic acid (DHICA) are the main monomer units of eumelanin, the black to brown pigment in humans, and have emerging biological roles beyond melanin. Elaboration of commercially available 5,6-dimethoxy-2-carboxylate ethyl ester provides ready access to DHICA-inspired small molecules, including 3-(hetero)aryl-indoles and 4,7-di-(hetero)aryl-indoles.

  二羟基吲哚如 5,6-二羟基吲哚-2-羧酸 (DHICA) 是真黑色素的主要单体单元，真黑色素是人体中的黑色至棕色色素，并具有超越黑色素的新兴生物学作用。市售的 5,6-二甲氧基-2-羧酸乙酯的研制提供了对 DHICA 启发的小分子的便捷访问，包括 3-(杂)芳基-吲哚和 4,7-二-(杂)芳基-吲哚。