N-(2-oxo-2-p-tolylethyl)-5,6-dihydroxy-1H-indole-2-carboxylic acid | 1380695-38-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2-oxo-2-p-tolylethyl)-5,6-dihydroxy-1H-indole-2-carboxylic acid
• 英文别名: N-(2-oxo-2-p-tolylethyl)-DHICA；5,6-Dihydroxy-1-[2-(4-methylphenyl)-2-oxoethyl]indole-2-carboxylic acid
• CAS: 1380695-38-4
• 化学式: C₁₈H₁₅NO₅
• 分子量: 325.321
• InChiKey: HZQATECBCJGZIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  99.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5,6-二甲氧基吲哚-2-甲酸乙酯 在 三溴化硼 、 lithium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(2-oxo-2-p-tolylethyl)-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

文献信息

• [EN] GPR35 LIGANDS AND THE USES THEREOF<br/>[FR] LIGANDS DE GPR35 ET LEURS UTILISATIONS
  申请人：CORNING INC

  公开号：WO2013022740A2

  公开（公告）日：2013-02-14

  Disclosed are compositions and methods for reducing the risk of and/or treatment of diseases which are pathophysiologically related to GPR35, and/or GPR35-hERG signaling complex. For example, disclosed are compounds for reducing the risk of and/or treating diseases which are pathophysiologically related to GPR35 in a subject.
• Synthesis and Agonistic Activity at the GPR35 of 5,6-Dihydroxyindole-2-carboxylic Acid Analogues
  作者：Huayun Deng、Ye Fang

  DOI：10.1021/ml300076u

  日期：2012.7.12

  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.