1,2-bis(2-carboxyl-1H-indol-5-yl)ethyne | 180526-03-8

• 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: 1,2-bis(2-carboxyl-1H-indol-5-yl)ethyne
• 英文别名: 5-[2-(2-carboxy-1H-indol-5-yl)ethynyl]-1H-indole-2-carboxylic acid
• CAS: 180526-03-8
• 化学式: C₂₀H₁₂N₂O₄
• 分子量: 344.326
• InChiKey: OCSFRIMVSXKXDO-UHFFFAOYSA-N

物化性质

• 沸点：
  782.3±55.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106.18
• 氢给体数：
  4.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl (8S)-8-(chloromethyl)-4-hydroxy-2-(trifluoromethyl)-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-1-carboxylate 、 1,2-bis(2-carboxyl-1H-indol-5-yl)ethyne 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 生成 methyl (8S)-8-(chloromethyl)-6-[5-[2-[2-[(8S)-8-(chloromethyl)-4-hydroxy-1-methoxycarbonyl-2-(trifluoromethyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-6-carbonyl]-1H-indol-5-yl]ethynyl]-1H-indole-2-carbonyl]-4-hydroxy-2-(trifluoromethyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate
  参考文献：
  名称：

  The novel cyclopropapyrroloindole(CPI) bisalkylators bearing methoxycarbonyl and trifluoromethyl groups

  摘要：

  The novel 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) bisalkylators were synthesized and their antitumor activity was evaluated. Among these derivatives, 7f in which two MCTFCPI moieties are connected with a 5,5'-bis(2-carbonyl-1 H-indole) group, was found to exhibit more prominent cytotoxicity and antitumor activity than U-77,779 (bizelesin) (2). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00235-2
• 作为产物：
  描述：

  5-溴吲哚-2-甲酸甲酯 在 氢氧化钾 、 sodium hydroxide 、 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 生成 1,2-bis(2-carboxyl-1H-indol-5-yl)ethyne
  参考文献：
  名称：

  The novel cyclopropapyrroloindole(CPI) bisalkylators bearing methoxycarbonyl and trifluoromethyl groups

  摘要：

  The novel 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) bisalkylators were synthesized and their antitumor activity was evaluated. Among these derivatives, 7f in which two MCTFCPI moieties are connected with a 5,5'-bis(2-carbonyl-1 H-indole) group, was found to exhibit more prominent cytotoxicity and antitumor activity than U-77,779 (bizelesin) (2). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00235-2