4-(1-methylindol-3-yl)-3-hydroxy-1H-pyrrole-2,5-dione | 197390-12-8

• 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: 4-(1-methylindol-3-yl)-3-hydroxy-1H-pyrrole-2,5-dione
• 英文别名: 3-hydroxy-4-(N-methylindol-3-yl)pyrrole-2,5-dione；3-Hydroxy-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione；3-hydroxy-4-(1-methylindol-3-yl)pyrrole-2,5-dione
• CAS: 197390-12-8
• 化学式: C₁₃H₁₀N₂O₃
• 分子量: 242.234
• InChiKey: OISDNEOLWOVHPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  71.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(1-methylindol-3-yl)-3-hydroxy-1H-pyrrole-2,5-dione 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 TEA 、 caesium bromide 、 sodium hydride 、 potassium carbonate 、 cesium fluoride 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 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
• 作为产物：
  描述：

  吲哚-3-乙腈 在 氢氧化钾 、 potassium tert-butylate 、 双氧水 、 potassium carbonate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 4-(1-methylindol-3-yl)-3-hydroxy-1H-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

• Neuroprotective and anti-proliferative compounds
  申请人：——

  公开号：US20040102467A1

  公开（公告）日：2004-05-27

  This invention features ring-substituted pyrrolo-&bgr;-carboline derivatives and ring-substitution and structural derivatives of 3-(1H-indol-3-yl)-1H-pyrrole-2,5-dione of formulas (I-III), which are useful as neuroprotective and anti-proliferative compounds. Also disclosed are methods for the preparation of these compounds, selected biological profiles and uses of these compounds in the treatment of various neurodegenerative and inflammatory diseases of the human nervous system and in the treatment of various other proliferative disorders characterized by loss of growth or cellular differentiation control including, but not limited to, cancer and inflammation. 1

  这项发明涉及环取代吡咯β-咔啉衍生物和3-(1H-吲哚-3-基)-1H-吡咯-2,5-二酮的环取代和结构衍生物，其作为神经保护和抗增殖化合物具有用途。还公开了这些化合物的制备方法，选择的生物学特性以及这些化合物在治疗人类神经系统的各种神经退行性和炎症性疾病以及治疗其他各种增殖性疾病中的用途，这些疾病的特征是失去生长或细胞分化控制，包括但不限于癌症和炎症。
• Inhibition of hydrogen peroxide-induced necrotic cell death with 3-amino-2-indolylmaleimide derivatives
  作者：Kosuke Dodo、Miho Katoh、Tadashi Shimizu、Masahiro Takahashi、Mikiko Sodeoka

  DOI：10.1016/j.bmcl.2005.04.016

  日期：2005.6

  Novel analogs of indolylmaleimide derivatives (IM derivatives) were synthesized and tested for cell death-inhibitory activity. 2-(1H-Indol-3-yl)-3-pentylamino-maleimide IM-54 was the most effective cell death inhibitor among the compounds tested. IM-54 inhibited necrotic cell death induced by H2O2, but not apoptotic cell death induced by etoposide. These results indicated that this novel cell death inhibitor is distinct from the well-known caspase inhibitor, Z-VAD, which can block apoptotic cell death, but not necrotic cell death. IM-54 is expected to be a powerful bioprobe for clarifying the unique signaling pathway of necrotic cell death. (c) 2005 Elsevier Ltd. All rights reserved.
• Anilino-monoindolylmaleimides as potent and selective JAK3 inhibitors
  作者：Mark E. McDonnell、Haiyan Bian、Jay Wrobel、Garry R. Smith、Shuguang Liang、Haiching Ma、Allen B. Reitz

  DOI：10.1016/j.bmcl.2014.01.001

  日期：2014.2

  We designed a series of anilino-indoylmaleimides based on structural elements from literature JAK3 inhibitors 3 and 4, and our lead 5. These new compounds were tested as inhibitors of JAKs 1, 2 and 3 and TYK2 for therapeutic intervention in rheumatoid arthritis (RA). Our requirements, based on current scientific rationale for optimum efficacy against RA with reduced side effects, was for potent, mixed JAK1 and 3 inhibition, and selectivity over JAK2. Our efforts yielded a potent JAK3 inhibitor 11d and its eutomer 11e. These compounds were highly selective for inhibition of JAK3 over JAK2 and TYK. The compounds displayed only modest JAK1 inhibition. (C) 2014 Elsevier Ltd. All rights reserved.
• EP0888339A4
  申请人：——

  公开号：EP0888339A4

  公开（公告）日：2001-02-28
• SYNTHESIS OF INDOLYLMALEIMIDES
  申请人：ELI LILLY AND COMPANY

  公开号：EP0888339A1

  公开（公告）日：1999-01-07