2,3-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: 2,3-dimethoxyindeno[1,2-b]indol-10(5H)-one
• 英文别名: 2,3-Dimethoxy-indeno[1,2-b]indol-10(5H)-one；2,3-dimethoxy-5H-indeno[1,2-b]indol-10-one
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: WVWQYENBQSWXHR-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：

  2,3-dimethoxyindeno[1,2-b]indol-10(5H)-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 2,3-dimethoxy-5,10-dihydroindeno[1,2-b]indol-10-ol
  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：

  5,6-二甲氧基茚酮 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 2,3-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

• Indenoindolone compounds
  申请人：——

  公开号：US20020173531A1

  公开（公告）日：2002-11-21

  Compound of formula (I): 1 wherein: R represents hydrogen or a group selected from alkenyl and optionally substituted alkyl, each of R 1 to R 8 , which may be identical or different, represents hydrogen or a group selected from alkyl, alkenyl, hydroxy, alkoxy, alkenyloxy, arylalkyl, arylalkoxy, carboxy, acyloxy and arylcarbonyloxy, or one of R 1 to R 8 forms with an adjacent one R 1 to R 8 an alkylenedioxy group, its optical isomers when they exist, and addition salts thereof with a pharmaceutically acceptable acid or base, with the proviso that: when R does not represent hydrogen, then at least one of R 1 to R 8 represents hydroxy or acyloxy, and the compounds of formula (I) are other than indeno[1,2-b]indol-10(5H)-one. Medicinal products containing the same which are useful for treatment of disorders of the melatoninergic system.

  化合物的化学式（I）如下：其中：R代表氢或从烯基和可选择的取代烷基中选择的基团，R1到R8中的每一个，可能相同也可能不同，代表氢或从烷基、烯基、羟基、烷氧基、烯基氧基、芳基烷基、芳基氧基、羧基、酰氧基和芳基羰氧基中选择的基团，或者R1到R8中的一个与相邻的R1到R8形成烷二氧基基团，其光学异构体（存在时）及其与药学上可接受的酸或碱形成的加合物，但条件是：当R不代表氢时，那么至少R1到R8中的一个代表羟基或酰氧基，化合物的化学式（I）不包括吲哚[1,2-b]吲哚-10(5H)-酮。含有该化合物的药物用于治疗褪黑素系统紊乱。
• 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.
• 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.
• Dérivés d'indénoindolones, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：Les Laboratoires Servier

  公开号：EP1266887B1

  公开（公告）日：2005-08-17