2,6-bis[2-(3-methylbutyl)indol-3-yl]-3,5-dibromocyclohexa-2,5-diene-1,4-dione

• 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: 2,6-bis[2-(3-methylbutyl)indol-3-yl]-3,5-dibromocyclohexa-2,5-diene-1,4-dione
• 英文别名: 2,6-dibromo-3,5-bis[2-(3-methylbutyl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione
• 化学式: C₃₂H₃₂Br₂N₂O₂
• 分子量: 636.426
• InChiKey: AZWIQRDWTWEMCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  65.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  四溴对苯醌 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 25.5h， 生成 2,6-bis[2-(3-methylbutyl)indol-3-yl]-3,5-dibromocyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  A One-Pot, Two-Step Synthesis of Tetrahydro Asterriquinone E

  摘要：

  Bis(indolyl)dihydroxyquinone 2, the tetrahydro analogue of naturally occurring 1a, was synthesized by a novel, expeditious route. The short synthesis was accomplished by treating p-bromanil (3) with 2 equiv of indole 4 in the presence of cesium carbonate in acetonitrile at ambient temperature to provide a 1:1 mixture of the dibromo regioisomers 7 and 8, followed by hydrolysis of the mixture to afford 2, The synthetic compound 2 was found to inhibit the binding of the Grb2 adapter protein to tyrosine-phosphorylated EGF receptor (IC50 = 1.2 mu M).

  DOI：

  10.1021/ol990075b

文献信息

• Methods of using bis-indolylquinones
  申请人：——

  公开号：US20030060635A1

  公开（公告）日：2003-03-27

  The present invention relates to novel synthetic methods for the preparation of indolylquinones. The methods of the present invention are directed to synthetic reactions involving indoles and halo-quinones in solvent and in the presence of a metal carbonate. The invention also relates to bis- and mono-indolylquinones of high purity and pharmaceutical compositions containing the same.

  本发明涉及一种制备吲哚基喹酮的新型合成方法。本发明的方法涉及在溶剂中和金属碳酸盐的存在下，将吲哚和卤代喹酮进行合成反应。本发明还涉及高纯度的双吲哚基喹酮和单吲哚基喹酮以及包含它们的药物组合物。
• Bis-indolyquinone compounds
  申请人：——

  公开号：US20020156116A1

  公开（公告）日：2002-10-24

  The present invention relates to a class of indolylquinone compounds that inhibit GRB-2 adaptor protein function, pharmaceutical compositions comprising these compounds, and methods for ameliorating the symptoms of cell proliferative disorders associated with GRB-2 adaptor protein function using these compounds. The present invention further relates to methods for treating insulin-related disorders, such as diabetes, insulin resistance, insulin deficiency and insulin allergy, and for ameliorating the symptoms of insulin-related disorders, using certain indolylquinone compounds and pharmaceutical compositions thereof. The present invention also relates to novel synthetic methods for the preparation of mono- and bis-indolylquinone compounds.

  本发明涉及一类抑制GRB-2适配蛋白功能的吲哚基喹啉化合物，包括这些化合物的制药组合物以及使用这些化合物改善与GRB-2适配蛋白功能相关的细胞增殖性疾病症状的方法。本发明还涉及使用某些吲哚基喹啉化合物及其制药组合物治疗胰岛素相关疾病，如糖尿病、胰岛素抵抗、胰岛素缺乏和胰岛素过敏，并改善胰岛素相关疾病症状的方法。本发明还涉及新的合成方法，用于制备单吲哚基喹啉化合物和双吲哚基喹啉化合物。
• SYNTHETIC METHODS FOR THE PREPARATION OF INDOLYLQUINONES AND MONO- AND BIS-INDOLYLQUINONES PREPARED THEREFROM
  申请人：Sugen, Inc.

  公开号：EP0959881B1

  公开（公告）日：2005-09-21
• EP0959881A4
  申请人：——

  公开号：EP0959881A4

  公开（公告）日：2001-06-27
• MONO- AND BIS-INDOLYLQUINONES AND PROPHYLACTIC AND THERAPEUTIC USES THEREOF
  申请人：Sugen, Inc.

  公开号：EP1218342A2

  公开（公告）日：2002-07-03