5,6-dimethoxy-3-phenyl-indole-2-carboxylic acid | 859075-88-0

• 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
• 英文名称: 5,6-dimethoxy-3-phenyl-indole-2-carboxylic acid
• 英文别名: 5,6-Dimethoxy-3-phenyl-indol-2-carbonsaeure；5,6-dimethoxy-3-phenyl-1H-indole-2-carboxylic Acid
• CAS: 859075-88-0
• 化学式: C₁₇H₁₅NO₄
• 分子量: 297.31
• InChiKey: WNEPZYOYIRGIQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-dimethoxy-3-phenyl-indole-2-carboxylic acid 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 5,6-dihydroxy-3-phenyl-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：

  5,6-二甲氧基吲哚-2-甲酸乙酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-溴代丁二酰亚胺(NBS) 、 水 、 sodium carbonate 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 5,6-dimethoxy-3-phenyl-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

• Indole and Azaindole Derivatives with Antitumor Action
  申请人：Farina Carlo

  公开号：US20070248672A1

  公开（公告）日：2007-10-25

  Indole and azaindole compounds useful for the treatment of solid tumours and tumours of the blood are described, they being particularly effective in the treatment of drug resistant tumours; these compounds are also able to synergistically enhance the activity of known antitumour drugs. They can hence be used either alone as antitumour agents or in association with known antitumour drugs. Processes for preparing the aforesaid compounds, which are partly new, and pharmaceutical compositions useful for the aforesaid treatments are also described.

  本文描述了用于治疗实体肿瘤和血液肿瘤的吲哚和氮杂吲哚化合物，它们在治疗耐药性肿瘤方面特别有效；这些化合物还能够协同增强已知抗肿瘤药物的活性。因此，它们可以作为单独的抗肿瘤剂使用，也可以与已知的抗肿瘤药物联合使用。本文还描述了制备上述部分新化合物的过程以及用于上述治疗的制药组合物。
• Beer et al., Journal of the Chemical Society, 1949, p. 2061,2064
  作者：Beer et al.

  DOI：——

  日期：——
• Lions; Spruson, Journal and Proceedings - Royal Society of New South Wales, 1932, vol. 66, p. 171,178
  作者：Lions、Spruson

  DOI：——

  日期：——
• INDOLE AND AZAINDOLE DERIVATIVES WITH ANTITUMOR ACTION
  申请人：NIKEM RESEARCH S.R.L.

  公开号：EP1750687A2

  公开（公告）日：2007-02-14
• INDOLE AND AZAINDOLE DERIVATIVES FOR THE TREATMENT OF INFLAMMATORY AND AUTOIMMUNE DISEASES
  申请人：BRANE DISCOVERY S.R.L.

  公开号：EP1945305A2

  公开（公告）日：2008-07-23