2-chloro-11-oxo-11H-indeno[1,2-b]quinoline-6-carboxylic acid | 214637-83-9

• 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-chloro-11-oxo-11H-indeno[1,2-b]quinoline-6-carboxylic acid
• 英文别名: 2-Chloro-11-oxoindeno[1,2-b]quinoline-6-carboxylic acid
• CAS: 214637-83-9
• 化学式: C₁₇H₈ClNO₃
• 分子量: 309.708
• InChiKey: KCXWVBVFOQONRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-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 23.0h， 生成 2-Chloro-11-oxo-11H-indeno[1,2-b]quinoline-6-carboxylic acid (2-dimethylamino-ethyl)-amide
  参考文献：
  名称：

  Ring-substituted 11-oxo-11H-indeno[1,2-b]quinoline-6-carboxamides with similar patterns of cytotoxicity to the dual topo I/II inhibitor DACA

  摘要：

  A series of ring-substituted analogues of the topoisomerase inhibitor 11-oxo-11H-indeno[1,2-b]quinoline-6-carboxamides was prepared and evaluated. The compounds were prepared by Pfitzinger reaction of the appropriate isatin-7-carboxylic acids and 1-indanones, followed by selective thermal decarboxylation of the resulting tetracyclic diacids, subsequent oxidation of the methylene group with alkaline permanganate under carefully controlled conditions, and 1,1'-carbonyldiimidazole-induced amidation. The compounds were evaluated in a panel of cell lines in culture. The largest increases in cytotoxicity (five to tenfold) were shown by 4-substituted analogues, with the 4-Cl derivative having an IC50 of 8 nM against the Lewis lung carcinoma. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00231-x
• 作为产物：
  描述：

  2,3-二氧吲哚林-7-羧酸 在 sodium hydroxide 、 potassium permanganate 、 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 55.0~300.0 ℃ 、66.66 Pa 条件下， 反应 3.25h， 生成 2-chloro-11-oxo-11H-indeno[1,2-b]quinoline-6-carboxylic acid
  参考文献：
  名称：

  Ring-substituted 11-oxo-11H-indeno[1,2-b]quinoline-6-carboxamides with similar patterns of cytotoxicity to the dual topo I/II inhibitor DACA

  摘要：

  A series of ring-substituted analogues of the topoisomerase inhibitor 11-oxo-11H-indeno[1,2-b]quinoline-6-carboxamides was prepared and evaluated. The compounds were prepared by Pfitzinger reaction of the appropriate isatin-7-carboxylic acids and 1-indanones, followed by selective thermal decarboxylation of the resulting tetracyclic diacids, subsequent oxidation of the methylene group with alkaline permanganate under carefully controlled conditions, and 1,1'-carbonyldiimidazole-induced amidation. The compounds were evaluated in a panel of cell lines in culture. The largest increases in cytotoxicity (five to tenfold) were shown by 4-substituted analogues, with the 4-Cl derivative having an IC50 of 8 nM against the Lewis lung carcinoma. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00231-x