5-benzyl-4b,9b-dihydroxy-4b,5,6,7,8,9b-hexahydroindeno[1,2-b]indole-9,10-dione | 1158819-73-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-benzyl-4b,9b-dihydroxy-4b,5,6,7,8,9b-hexahydroindeno[1,2-b]indole-9,10-dione
• CAS: 1158819-73-8
• 化学式: C₂₂H₁₉NO₄
• 分子量: 361.397
• InChiKey: IGHHCXUYUOWFDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  77.84
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-benzyl-4b,9b-dihydroxy-4b,5,6,7,8,9b-hexahydroindeno[1,2-b]indole-9,10-dione 在 sodium tetrahydroborate 、 硫酸 、 溶剂黄146 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 0.75h， 生成 11-benzyl-7-hydroxy-8,9,10,11-tetrahydro-7H-6-oxa-11-aza-benzo[a]fluoren-5-one
  参考文献：
  名称：

  Synthesis of 4-hydroxyindole fused isocoumarin derivatives and their fluorescence “Turn-off” sensing of Cu(ii) and Fe(iii) ions

  摘要：

  已经开发了一种简单高效的协议，用于从易得的起始材料合成4-羟基吲哚并噻吩酮。

  DOI：

  10.1039/c5ra01060h
• 作为产物：
  描述：

  水合茚三酮 、 N-benzyl-3-amino-2-cyclohexen-1-one 以85%的产率得到5-benzyl-4b,9b-dihydroxy-4b,5,6,7,8,9b-hexahydroindeno[1,2-b]indole-9,10-dione
  参考文献：
  名称：

  Partially Saturated Indeno[1,2-b]indole Derivatives via Deoxygenation of Heterocyclic α-Hydroxy-N,O-hemiaminals

  摘要：

  一系列3-氨基环己烯-2-酮与单水合的吡喃-1,2,3-三酮（呋喃啉）反应，生成4b,9b-二羟基吲哚[1,2-b]吲哚，其后经脱氧反应转化为吲哚[1,2-b]吲哚。

  DOI：

  10.1055/s-0028-1087983

文献信息

• Lactic acid-catalyzed fusion of ninhydrin and enamines for the solvent-free synthesis of hexahydroindeno[1,2-<i>b</i>]indole-9,10-diones
  作者：Xuwen Chen、Yunyun Liu

  DOI：10.1515/hc-2016-0048

  日期：2016.6.1

  The lactic acid-catalyzed reactions of ninhydrin and secondary enaminones were conducted by solvent-free grinding at room temperature to yield polycyclic 4b,9b-dihydroxy-4b,5,6,7,8,9b-hexahydroindeno[1,2-b]indole-9,10-diones.

  标题：摘要 在室温下无溶剂研磨的情况下，以乳酸为催化剂，对尼因醛和次级烯酮进行反应，得到多环4b,9b-二羟基-4b,5,6,7,8,9b-六氢吲哚并[1,2-b]吲哚-9,10-二酮。
• Indeno[1,2-b]indole derivatives as a novel class of potent human protein kinase CK2 inhibitors
  作者：Claas Hundsdörfer、Hans-Jörg Hemmerling、Claudia Götz、Frank Totzke、Patrick Bednarski、Marc Le Borgne、Joachim Jose

  DOI：10.1016/j.bmc.2012.02.017

  日期：2012.4

  Herein we describe the synthesis and properties of indeno[1,2-b]indole derivatives as a novel class of potent inhibitors of the human protein kinase CK2. A set of 19 compounds was obtained using a convenient and straightforward synthesis protocol. The compounds were tested for inhibition of human protein kinase CK2, which was recombinantly expressed in Escherichia coli. New inhibitors with IC50 in the micro-

  在这里，我们描述了茚并[1,2- b ]吲哚衍生物的合成及其性质，它们是一类新型的人类蛋白激酶CK2的有效抑制剂。使用方便和直接的合成方案获得了一组19种化合物。测试了化合物对在大肠杆菌中重组表达的人蛋白激酶CK2的抑制作用。鉴定出IC 50在微摩尔和亚微摩尔范围内的新抑制剂。化合物4b（5-异丙基-7,8-二氢茚并[1,2- b ]吲哚-9,10（5 H，6 H）-二酮）抑制人CK2的IC 50浓度为0.11μM，并且没有显着抑制22种其他人类蛋白激酶，表明对CK2具有选择性。显示了化合物4b对ATP的竞争抑制作用，确定的K i为0.06μM。我们的发现表明，茚并[1,2- b ]吲哚是进一步开发和优化人类蛋白激酶CK2抑制剂的有希望的起点。
• Novel indeno[1,2-b]indoloquinones as inhibitors of the human protein kinase CK2 with antiproliferative activity towards a broad panel of cancer cell lines
  作者：Claas Hundsdörfer、Hans-Jörg Hemmerling、Janina Hamberger、Marc Le Borgne、Patrick Bednarski、Claudia Götz、Frank Totzke、Joachim Jose

  DOI：10.1016/j.bbrc.2012.06.068

  日期：2012.7

  We previously reported indeno[1,2-b]indoles as a novel class of potent inhibitors of the human protein kinase CK2. In the present study we prepared two novel quinoid derivatives, the indeno[1,2-b]indoloquinones 6b and 6c, and demonstrated inhibition of the human CK2 by the compounds. Furthermore, we showed substantial antiproliferative activity of both compounds towards a broad panel of human cancer cell lines in the low micromolar range. Whereas the earlier indeno[1,2-b]indoles have been shown to be selective for CK2, the indeno[1,2-b]indoloquinones 6b and 6c also inhibited the AMPK activated protein kinase ARK5, potentially contributing to the anti-cancer effects of the compounds. In addition, with compound 6b we found a very potent inhibitor of the leukemia-associated receptor tyrosine kinase FLT3, with an IC50 of 0.18 mu M. (C) 2012 Elsevier Inc. All rights reserved.