2,3,4-trimethoxy-11H-indeno[1,2-b]quinoline-6-carboxylic acid | 253120-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,3,4-trimethoxy-11H-indeno[1,2-b]quinoline-6-carboxylic acid
• CAS: 253120-53-5
• 化学式: C₂₀H₁₇NO₅
• 分子量: 351.359
• InChiKey: PSZVLYGVGOUWKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  77.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4-trimethoxy-11H-indeno[1,2-b]quinoline-6-carboxylic acid 在 potassium permanganate 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 16.03h， 生成 2,3,4-Trimethoxy-11-oxo-11H-indeno[1,2-b]quinoline-6-carboxylic acid (2-dimethylamino-ethyl)-amide
  参考文献：
  名称：

  Synthesis of Substituted Indeno[1,2-b]quinoline-6-carboxamides, [1]benzothieno[3,2-b]quinoline-4-carboxamides and 10H-quindoline-4-carboxamides: Evaluation of Structure–Activity Relationships for Cytotoxicity

  摘要：

  New substituted indeno[1,2-b]quinoline-6-carboxamides, [1]benzothieno[3,2-b]quinoline-4-carboxamides and 10H-quindoline-4-carboxamides were prepared from methyl 2-amino-3-formylbenzoate by a new Friedlander synthesis. Evaluation of these carboxamides for cytotoxicity in a panel of cell lines showed that small lipophilic substituents in the non-carboxamide ring, in a pseudo-peri position to the side chain, significantly increased cytotoxic potency while retaining a pattern of cytotoxicity consistent with a non-topo II mode of action. The methyl substituted indeno[1,2-b]quinoline-6-carboxamide demonstrated substantial effectiveness (20-day growth delays) in a sub-cutaneous colon 38 in vivo tumor model. This is comparable to that reported for the dual topo I/II inhibitor DACA that is in clinical trial. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00179-6
• 作为产物：
  描述：

  靛红-7-甲酸甲酯 在 manganese(IV) oxide 、 sodium hydroxide 、 sodium tetrahydroborate 、 potassium tert-butylate 、 双氧水 作用下， 以 四氢呋喃 、 氯仿 、 水 、 叔丁醇 为溶剂， 反应 4.17h， 生成 2,3,4-trimethoxy-11H-indeno[1,2-b]quinoline-6-carboxylic acid
  参考文献：
  名称：

  2-氨基-3-甲酰基苯甲酸甲酯的制备及其在弗里德兰德合成中的应用

  摘要：

  摘要 标题化合物由 7-羧酸甲酯经四步制备。与 1-茚满酮和类似物缩合得到 11H-茚并[1,2-b]喹啉-6-羧酸，与环己酮缩合得到吖啶-4-羧酸。

  DOI：

  10.1080/00397919908085895

文献信息

• A Preparation Of Methyl 2-amino-3-formylbenzoate and its use in Friedlander Synthesis
  作者：Xianyong Bu、Leslie W. Deady

  DOI：10.1080/00397919908085895

  日期：1999.12.1

  Abstract The title compound has been prepared in four steps from methyl isatin-7-carboxylate. Condensations with 1-indanone and analogs gave 11H-indeno[1,2-b]quinoline-6-carboxylic acids, and with cyclohexanones gave acridine-4-carboxylic acids.

  摘要 标题化合物由 7-羧酸甲酯经四步制备。与 1-茚满酮和类似物缩合得到 11H-茚并[1,2-b]喹啉-6-羧酸，与环己酮缩合得到吖啶-4-羧酸。
• Synthesis of Substituted Indeno[1,2-b]quinoline-6-carboxamides, [1]benzothieno[3,2-b]quinoline-4-carboxamides and 10H-quindoline-4-carboxamides: Evaluation of Structure–Activity Relationships for Cytotoxicity
  作者：Junjie Chen、Leslie W. Deady、José Desneves、Anthony J. Kaye、Graeme J. Finlay、Bruce C. Baguley、William A. Denny

  DOI：10.1016/s0968-0896(00)00179-6

  日期：2000.10

  New substituted indeno[1,2-b]quinoline-6-carboxamides, [1]benzothieno[3,2-b]quinoline-4-carboxamides and 10H-quindoline-4-carboxamides were prepared from methyl 2-amino-3-formylbenzoate by a new Friedlander synthesis. Evaluation of these carboxamides for cytotoxicity in a panel of cell lines showed that small lipophilic substituents in the non-carboxamide ring, in a pseudo-peri position to the side chain, significantly increased cytotoxic potency while retaining a pattern of cytotoxicity consistent with a non-topo II mode of action. The methyl substituted indeno[1,2-b]quinoline-6-carboxamide demonstrated substantial effectiveness (20-day growth delays) in a sub-cutaneous colon 38 in vivo tumor model. This is comparable to that reported for the dual topo I/II inhibitor DACA that is in clinical trial. (C) 2000 Elsevier Science Ltd. All rights reserved.