5,6,7-trimethoxyisoquinoline-3-carboxylic acid methyl ester | 224321-86-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 5,6,7-trimethoxyisoquinoline-3-carboxylic acid methyl ester
• 英文别名: Methyl 5,6,7-trimethoxyisoquinoline-3-carboxylate
• CAS: 224321-86-2
• 化学式: C₁₄H₁₅NO₅
• 分子量: 277.277
• InChiKey: ZNCUGYYLBUKXLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,6,7-trimethoxyisoquinoline-3-carboxylic acid methyl ester 在 氢氧化钾 、 乙醇 作用下， 反应 2.5h， 以83%的产率得到5,6,7-trimethoxyisoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Novel Cyclopropapyrroloindole Derivative (AT-3510) Bearing Methoxycarbonyl and Trifluoromethyl Groups

  摘要：

  The seco-Cl 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) derivatives dl- and/or (S)-10 carrying various acyl moieties at the NG-position were synthesized along with their prodrugs (S)-12, and their antitumor activity was evaluated. Among these derivatives, AT-3510 [(S)-12m], the novel prodrug MCTFCPI derivative carrying a 5-(7-methoxybenzofuran-2-ylcarbonyl)aminoindole-2-carbonyl group at the NG-position, was found to exhibit more excellent antitumor activity against human tumor xenografts than the clinical trial candidates carzelesin (6) and KW-2189 (7) and cisplatin.

  DOI：

  10.1021/jm980668c
• 作为产物：
  描述：

  2,3,4-三甲氧基-6-甲基苯甲醛 在 甲醇 、 sodium 作用下， 以 xylene 为溶剂， 反应 27.0h， 生成 5,6,7-trimethoxyisoquinoline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Novel Cyclopropapyrroloindole Derivative (AT-3510) Bearing Methoxycarbonyl and Trifluoromethyl Groups

  摘要：

  The seco-Cl 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) derivatives dl- and/or (S)-10 carrying various acyl moieties at the NG-position were synthesized along with their prodrugs (S)-12, and their antitumor activity was evaluated. Among these derivatives, AT-3510 [(S)-12m], the novel prodrug MCTFCPI derivative carrying a 5-(7-methoxybenzofuran-2-ylcarbonyl)aminoindole-2-carbonyl group at the NG-position, was found to exhibit more excellent antitumor activity against human tumor xenografts than the clinical trial candidates carzelesin (6) and KW-2189 (7) and cisplatin.

  DOI：

  10.1021/jm980668c