2,3-Dimethoxy-5-methylindeno[1,2-b]indol-10-one | 1384523-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,3-Dimethoxy-5-methylindeno[1,2-b]indol-10-one
• 英文别名: 2,3-dimethoxy-5-methylindeno[1,2-b]indol-10-one
• CAS: 1384523-05-0
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: NJVJPYJRYCMOIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-Dimethoxy-5-methylindeno[1,2-b]indol-10-one 在 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 2,3-dimethoxy-5-methylindeno[1,2-b]indol-10(5H)-one oxime
  参考文献：
  名称：

  Indenoindolone derivatives as topoisomerase II–inhibiting anticancer agents

  摘要：

  Based on known heterocyclic topoisomerase II inhibitors and anticancer agents, various indenoindolone derivatives were predicted as potential topoisomerase II-inhibiting anticancer agents. They are hydrazones, (thio)semicarbazones, and oximes of indenoindolones, and indenoindolols. These derivatives with suitable substitutions exhibited potent specific inhibition of human DNA TopoII alpha, while not showing inhibition of topoisomerase I and DNA intercalation, despite the fact that parent indenoindolones are known poor/moderate inhibitors of topoisomerase II. The potent topoisomerase II inhibitor indenoindolone derivatives exhibited good anticancer activities compared to etoposide and 5-fluorouracil, and relatively low toxicity to normal cells. These derivatizations of indenoindolones were found to result in enhancement of anticancer activities. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.063
• 作为产物：
  描述：

  在 氧气 、 palladium diacetate 、 potassium carbonate 、 三甲基乙酸 作用下， 反应 30.0h， 以71%的产率得到2,3-Dimethoxy-5-methylindeno[1,2-b]indol-10-one
  参考文献：
  名称：

  Intramolecular oxidative coupling of 3-indolylarylketones with Pd(II)-catalysis under air: convenient access to indenoindolones

  摘要：

  A Pd-catalyzed method has been developed for the intramolecular oxidative coupling of 3-indolylarylketones under open air as terminal oxidant toward the synthesis of indeno[1,2-b]indol-10(5H)-ones. This reaction represents an intramolecular coupling with dual activation of C-H bonds for electron-deficient arenes, while such reactions are common for electron-rich arenes. Pd(II)-catalysis with pivalic acid as co-catalyst has been found to be crucial. The reaction undergoes without indole N-H-protection. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.076

文献信息

• Intramolecular oxidative coupling of 3-indolylarylketones with Pd(II)-catalysis under air: convenient access to indenoindolones
  作者：Sankar K. Guchhait、Maneesh Kashyap、Somnath Kandekar

  DOI：10.1016/j.tetlet.2012.05.076

  日期：2012.7

  A Pd-catalyzed method has been developed for the intramolecular oxidative coupling of 3-indolylarylketones under open air as terminal oxidant toward the synthesis of indeno[1,2-b]indol-10(5H)-ones. This reaction represents an intramolecular coupling with dual activation of C-H bonds for electron-deficient arenes, while such reactions are common for electron-rich arenes. Pd(II)-catalysis with pivalic acid as co-catalyst has been found to be crucial. The reaction undergoes without indole N-H-protection. (C) 2012 Elsevier Ltd. All rights reserved.
• Indenoindolone derivatives as topoisomerase II–inhibiting anticancer agents
  作者：Maneesh Kashyap、Somnath Kandekar、Ashish T. Baviskar、Dipon Das、Ranjan Preet、Purusottam Mohapatra、Shakti Ranjan Satapathy、Sumit Siddharth、Sankar K. Guchhait、Chanakya N. Kundu、Uttam C. Banerjee

  DOI：10.1016/j.bmcl.2012.12.063

  日期：2013.2

  Based on known heterocyclic topoisomerase II inhibitors and anticancer agents, various indenoindolone derivatives were predicted as potential topoisomerase II-inhibiting anticancer agents. They are hydrazones, (thio)semicarbazones, and oximes of indenoindolones, and indenoindolols. These derivatives with suitable substitutions exhibited potent specific inhibition of human DNA TopoII alpha, while not showing inhibition of topoisomerase I and DNA intercalation, despite the fact that parent indenoindolones are known poor/moderate inhibitors of topoisomerase II. The potent topoisomerase II inhibitor indenoindolone derivatives exhibited good anticancer activities compared to etoposide and 5-fluorouracil, and relatively low toxicity to normal cells. These derivatizations of indenoindolones were found to result in enhancement of anticancer activities. (C) 2012 Elsevier Ltd. All rights reserved.