11H-indeno[1,2-b]quinoline-10-carboxylic acid | 98030-19-4

• 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: 11H-indeno[1,2-b]quinoline-10-carboxylic acid
• 英文别名: 11H-indeno[1,2-b]quinoline-10-carboxylic acid；11H-Indeno[1,2-b]chinolin-10-carbonsaeure；11H-Indeno<1,2-b>chinolin-10-carbonsaeure
• CAS: 98030-19-4
• 化学式: C₁₇H₁₁NO₂
• 分子量: 261.28
• InChiKey: VVCCVYMFSIACNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  11H-indeno[1,2-b]quinoline-10-carboxylic acid 在 联苯 作用下， 生成 11H-indeno[1,2-b]quinoline
  参考文献：
  名称：

  Huisgen; Ugi, Justus Liebigs Annalen der Chemie, 1957, vol. 610, p. 57,64

  摘要：

  DOI：
• 作为产物：
  描述：

  靛红 、 1-茚酮 反应 7.0h， 以81%的产率得到11H-indeno[1,2-b]quinoline-10-carboxylic acid
  参考文献：
  名称：

  Positioning of the Carboxamide Side Chain in 11-Oxo-11 H -indeno[1,2- b ]quinolinecarboxamide Anticancer Agents: Effects on Cytotoxicity

  摘要：

  A series of 11-oxo-11H-indeno[1,2-b]quinolines bearing a carboxamide-linked cationic side chain at various positions on the chromophore was studied to determine structure-activity relationships between cytotoxicity and the position of the side chain. The compounds were prepared by Pfitzinger synthesis from an appropriate isatin and 1-indanone, followed by various oxidative steps, to generate the required carboxylic acids. The 4- and 6-carboxamides (with the side chain on a terminal ring, off the short axis of the chromophore) were effective cytotoxins. The dimeric 4- and 6-linked analogues were considerably more cytotoxic than the parent monomers, but had broadly similar activities. In contrast, analogues with side chains at the 8-position ton a terminal ring but off the long axis of the chromophore) or 10-position (off the short axis of the chromophore but in a central ring) were drastically less effective. The 4,10- and 6,10-biscarboxamides had activities between those of the corresponding parent monocarboxamides. The first of these showed good activity against advanced subcutaneous colon 38 tumours in mice. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00264-9

文献信息

• Noelting; Herzbaum, Chemische Berichte, 1911, vol. 44, p. 2589
  作者：Noelting、Herzbaum

  DOI：——

  日期：——
• Huisgen; Ugi, Justus Liebigs Annalen der Chemie, 1957, vol. 610, p. 57,64
  作者：Huisgen、Ugi

  DOI：——

  日期：——
• Positioning of the Carboxamide Side Chain in 11-Oxo-11 H -indeno[1,2- b ]quinolinecarboxamide Anticancer Agents: Effects on Cytotoxicity
  作者：Leslie W. Deady、José Desneves、Anthony J. Kaye、Graeme J. Finlay、Bruce C. Baguley、William A. Denny

  DOI：10.1016/s0968-0896(00)00264-9

  日期：2001.2

  A series of 11-oxo-11H-indeno[1,2-b]quinolines bearing a carboxamide-linked cationic side chain at various positions on the chromophore was studied to determine structure-activity relationships between cytotoxicity and the position of the side chain. The compounds were prepared by Pfitzinger synthesis from an appropriate isatin and 1-indanone, followed by various oxidative steps, to generate the required carboxylic acids. The 4- and 6-carboxamides (with the side chain on a terminal ring, off the short axis of the chromophore) were effective cytotoxins. The dimeric 4- and 6-linked analogues were considerably more cytotoxic than the parent monomers, but had broadly similar activities. In contrast, analogues with side chains at the 8-position ton a terminal ring but off the long axis of the chromophore) or 10-position (off the short axis of the chromophore but in a central ring) were drastically less effective. The 4,10- and 6,10-biscarboxamides had activities between those of the corresponding parent monocarboxamides. The first of these showed good activity against advanced subcutaneous colon 38 tumours in mice. (C) 2001 Elsevier Science Ltd. All rights reserved.