2,4-dimethyl-11-oxo-11H-indeno[1,2-b]quinoline-6-carboxylic acid | 312273-18-0

• 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: 2,4-dimethyl-11-oxo-11H-indeno[1,2-b]quinoline-6-carboxylic acid
• CAS: 312273-18-0
• 化学式: C₁₉H₁₃NO₃
• 分子量: 303.317
• InChiKey: APPJONQXDPOXIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  67.26
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,4-dimethyl-11-oxo-11H-indeno[1,2-b]quinoline-6-carboxylic acid 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 2,4-Dimethyl-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：

  2,4-dimethyl-11H-indeno[1,2-b]quinoline-6-carboxylic acid 在 sodium dichromate 、 硫酸 作用下， 反应 3.0h， 以54%的产率得到2,4-dimethyl-11-oxo-11H-indeno[1,2-b]quinoline-6-carboxylic acid
  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