2,8-dimethoxyindeno[1,2-b]indol-10(5H)-one

• 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: 2,8-dimethoxyindeno[1,2-b]indol-10(5H)-one
• 英文别名: 2,8-dimethoxy-5H-indeno[1,2-b]indol-10-one
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: CEDOPAKFVNNIFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,8-dimethoxyindeno[1,2-b]indol-10(5H)-one 在 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 2,8-dimethoxyindeno[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：

  5-甲氧基-1-茚酮 在 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 3.5h， 生成 2,8-dimethoxyindeno[1,2-b]indol-10(5H)-one
  参考文献：
  名称：

  Facile Synthesis of Novel Indeno[1,2‐b]indol‐10‐one Derivatives by the Oxidation with DDQ

  摘要：

  The synthesis of indeno[1,2-b]indol-10-one analogues with a wide range of biological activities was described. They are also important intermediates of some selective estrogen receptor modulators (SERMs).

  DOI：

  10.1081/scc-200049795

文献信息

• Friedel-Crafts 3-(2-Bromobenzoylation) of Indoles and Intramolecular Direct Arylation: An Efficient Route to Indenoindolones
  作者：Sankar Guchhait、Maneesh Kashyap

  DOI：10.1055/s-0031-1289663

  日期：2012.2

  Friedel-Crafts reaction of 2-bromobenzoyl chlorides with indoles to give 3-(2-bromobenzoyl)indoles and their palladium-catalyzed intramolecular direct arylation to give indenoindolones, has been developed. 3-(2-Bromobenzoyl)indoles were crucial intermediates; the method was successful with N-unprotected or N-protected indoles. This approach affords a convenient preparation of diverse substituted and functionalized

  已经开发出一种有效的两步法，包括2-溴苯甲酰氯与吲哚的弗瑞德-克来福特反应，得到3-（2-溴苯甲酰基）吲哚，以及它们的钯催化的分子内直接芳基化，得到茚并吲哚酮。3-（2-溴苯甲酰基）吲哚是关键的中间体。该方法适用于N-未保护或N-保护的吲哚。该方法提供了从容易获得的起始原料以高收率到高收率方便地制备各种取代的和官能化的茚并吲哚酮的方法。通过该合成可以容易地掺入通常整合到生物活性化合物中的几个部分。 酰化-芳基化-催化-偶联-杂环-吲哚-路易斯酸-钯
• Scaffold hybridization in generation of indenoindolones as anticancer agents that induce apoptosis with cell cycle arrest at G2/M phase
  作者：Maneesh Kashyap、Dipon Das、Ranjan Preet、Purusottam Mohapatra、Shakti Ranjan Satapathy、Sumit Siddharth、Chanakya N. Kundu、Sankar K. Guchhait

  DOI：10.1016/j.bmcl.2012.02.007

  日期：2012.4

  Scaffold hybridization of several natural and synthetic anticancer leads led to the consideration of indenoindolones as potential novel anticancer agents. A series of these compounds were prepared by a diversity-feasible synthetic method. They were found to possess anticancer activities with higher potency compared to etoposide and 5-fluorouracil in kidney cancer cells (HEK 293) and low toxicity to corresponding normal cells (Vero). They exerted apoptotic effect with blocking of cell cycle at G2/M phase. (C) 2012 Elsevier Ltd. All rights reserved.