1-methyl-3-(1-methyl-1H-indol-3-yl)-4-(propylamino)-1H-pyrrole-2,5-dione

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-methyl-3-(1-methyl-1H-indol-3-yl)-4-(propylamino)-1H-pyrrole-2,5-dione
• 英文别名: IM-12；1-Methyl-3-(1-methylindol-3-yl)-4-(propylamino)pyrrole-2,5-dione；1-methyl-3-(1-methylindol-3-yl)-4-(propylamino)pyrrole-2,5-dione
• 化学式: C₁₇H₁₉N₃O₂
• 分子量: 297.357
• InChiKey: ARJFCWJMQZHXRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-chloro-3-(1H-indol-3-yl)-N-methylmaleimide 在 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-methyl-3-(1-methyl-1H-indol-3-yl)-4-(propylamino)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Inhibition of hydrogen peroxide-induced necrotic cell death with 3-amino-2-indolylmaleimide derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2005.04.016

文献信息

• Indolylmaleimide Derivative IM-17 Shows Cardioprotective Effects in Ischemia-Reperfusion Injury
  作者：Kosuke Dodo、Tadashi Shimizu、Jun Sasamori、Kazuyuki Aihara、Naoki Terayama、Shuhei Nakao、Katsuya Iuchi、Masahiro Takahashi、Mikiko Sodeoka

  DOI：10.1021/acsmedchemlett.7b00454

  日期：2018.3.8

  We previously developed IM-54 as a novel type of inhibitor of hydrogen-peroxide-induced necrotic cell death. Here, we examined its cell death inhibition profile. IM-54 was found to selectively inhibit oxidative stress-induced necrosis, but it did not inhibit apoptosis induced by various anticancer drugs or Fas ligand, or necroptosis. IM-17, an IM derivative having improved water-solubility and metabolic stability, was developed and confirmed to retain necrosis-inhibitory activity. IM-17 showed cardioprotective effects in an isolated rat heart model and an in vivo arrhythmia model, suggesting that IM derivatives may have therapeutic potential.
• 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.