3-(1H-indol-3-yl)-1-methyl-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione | 133053-46-0

• 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: 3-(1H-indol-3-yl)-1-methyl-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione
• 英文别名: 3-(1-methyl-3-indolyl)-4-(3-indolyl)-1-methyl-pyrrole-2,5-dione；4-(1-methyl-3-indolyl)-3-(1H-3-indolyl)-1-(methyl)-pyrrole-2,5-dione；3-(1H-indol-3-yl)-2-(1-methyl-1H-indol-3-yl)-N-methylmaleimide；3-(1H-indol-3-yl)-1-methyl-4-(1-methylindol-3-yl)pyrrole-2,5-dione
• CAS: 133053-46-0
• 化学式: C₂₂H₁₇N₃O₂
• 分子量: 355.396
• InChiKey: LZAZTAUNZFTSDO-UHFFFAOYSA-N

物化性质

• 熔点：
  205 °C
• 沸点：
  638.0±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  58.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1H-indol-3-yl)-1-methyl-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione 以79%的产率得到
  参考文献：
  名称：

  BARTH, H.;HARTENSTEIN, J.;BETCHE, H. -J.;SCHACHTELE, C.;RUDOLPH, C.;OSS. +

  摘要：

  DOI：
• 作为产物：
  描述：

  吲哚-3-乙腈 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 氢氧化钾 、 TEA 、 potassium tert-butylate 、 双氧水 、 caesium bromide 、 sodium hydride 、 potassium carbonate 、 cesium fluoride 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 25.0h， 生成 3-(1H-indol-3-yl)-1-methyl-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis of bisindolylmaleimides using a palladium catalyzed cross-coupling reaction

  摘要：

  Bisindolylmaleimides are known to be potent and selective PKC inhibitors. A new synthesis of this class of compound is reported. The key step is a Suzuki cross-coupling reaction using a readily available indolylmaleimide triflate intermediate. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(97)10174-3

文献信息

• Pyrrole derivatives and cell death inhibitors
  申请人：Sagami Chemical Research Center

  公开号：US06589977B1

  公开（公告）日：2003-07-08

  Bisindolylpyrrole derivatives represented by general formula [I] which are useful in inhibiting cell death and expected as being useful as preventives and remedies for the progress of various diseases in the progress and worsening of which cell death participates; and cell death inhibitors, drugs and cell/tissue/organ preservatives containing as the active ingredient these derivatives or pharmaceutically acceptable salts thereof.

  一般公式为[I]的双吲哚吡咯衍生物在抑制细胞死亡方面具有用处，并被期望作为预防和治疗各种疾病进展中细胞死亡参与的进展和恶化的药物；以及包含这些衍生物或其药学上可接受的盐作为活性成分的细胞死亡抑制剂、药物和细胞/组织/器官保护剂。
• Synthesis of indolylmaleimides
  申请人：Eli Lilly and Company

  公开号：US05859261A1

  公开（公告）日：1999-01-12

  The present invention provides a method for synthesizing indolylmaleimides by reacting an activated maleimide preferably with an optionally substituted organometallic-3-indole in the presence of a transition metal catalyst.

  本发明提供了一种合成吲哚马来酰亚胺的方法，该方法是通过在过渡金属催化剂的存在下，将活化的马来酰亚胺与可选地取代的有机金属-3-吲哚反应而得到的。
• Studies on cyclin-dependent kinase inhibitors: indolo-[2,3- a ]pyrrolo[3,4- c ]carbazoles versus bis-indolylmaleimides
  作者：Concha Sanchez-Martinez、Chuan Shih、Guoxin Zhu、Tiechao Li、Harold B. Brooks、Bharvin K.R. Patel、Richard M. Schultz、Tammy B. DeHahn、Charles D. Spencer、Scott A. Watkins、Catherine A. Ogg、Eileen Considine、Jack A. Dempsey、Faming Zhang

  DOI：10.1016/s0960-894x(03)00792-3

  日期：2003.11

  A series of indolo[2,3-a]pyrrolo[3,4-c]carbazoles and their bis-indolylmaleimides precursors have been prepared in order to compare their activity as D1-CDK4 inhibitors. Both enzymatic and antiproliferative assays have shown that the structurally more constrained indolo[2,3-a]pyrrolo[3,4-c]carbazoles are consistently more active (8-42-fold) in head-to-head comparison with their bis-indolylmaleimides

  为了比较它们作为D1-CDK4抑制剂的活性，已经制备了一系列的吲哚[2，3-a]吡咯并[3，4-c]咔唑及其双-吲哚基马来酰亚胺前体。酶促和抗增殖试验均表明，结构上更受约束的吲哚[2,3-a]吡咯并[3,4-c]咔唑与它们的二甲苯胺相比，头对头的活性始终更高（8-42倍）。 -indolylmaleimides同行。使用流式细胞术的细胞周期分析还显示，吲哚并咔唑是选择性的G1阻滞剂，而双吲哚基马来酰亚胺则将细胞阻滞在G2 / M期。
• PYRROLE DERIVATIVES AND CELL DEATH INHIBITORS
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP1152002A1

  公开（公告）日：2001-11-07

  Bisindolylpyrrole derivatives represented by general formula [I] which are useful in inhibiting cell death and expected as being useful as preventives and remedies for the progress of various diseases in the progress and worsening of which cell death participates; and cell death inhibitors, drugs and cell/tissue/organ preservatives containing as the active ingredient these derivatives or pharmaceutically acceptable salts thereof.

  由通式[I]表示的双吲哚基吡咯衍生物，可用于抑制细胞死亡，并可望作为预防和治疗细胞死亡导致的各种疾病的进展和恶化的药物；以及含有这些衍生物或其药学上可接受的盐类作为活性成分的细胞死亡抑制剂、药物和细胞/组织/器官防腐剂。
• Structure–activity relationship of N-methyl-bisindolylmaleimide derivatives as cell death inhibitors
  作者：Miho Katoh、Kosuke Dodo、Mikako Fujita、Mikiko Sodeoka

  DOI：10.1016/j.bmcl.2005.04.015

  日期：2005.6

  A series of N-methyl-bisindolylmaleimide derivatives was synthesized and evaluated as cell death inhibitors. N-Methyl-2[1-(3-aminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)maleimide (21) was the most potent inhibitor of H2O2-induced necrotic death of human leukemia HL60 cells among them. (c) 2005 Elsevier Ltd. All rights reserved.