IM-3 | 327602-15-3

• 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: IM-3
• 英文别名: 3-Chloro-1-methyl-4-(1-methylindol-3-yl)pyrrole-2,5-dione
• CAS: 327602-15-3
• 化学式: C₁₄H₁₁ClN₂O₂
• 分子量: 274.707
• InChiKey: QEPJLELSKUHBBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  IM-3 、 十四醇 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到1-Methyl-3-(1-methylindol-3-yl)-4-tetradecoxypyrrole-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
• 作为产物：
  描述：

  2-chloro-3-(1H-indol-3-yl)-N-methylmaleimide 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以88%的产率得到IM-3
  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

• Electrolyte composition and electrochemical battery using the same
  申请人：——

  公开号：US20020055046A1

  公开（公告）日：2002-05-09

  An electrolyte composition which is excellent in durability and charge transport performance, and an electrochemical battery in which deterioration of the charge transport performance with time is minimized, the electrolyte composition including therein a salt which comprises an anion which contains a mesogen group, and an alkyl or alkenyl group having 6 carbons or more in the structure of the anion, and an organic or inorganic cation.

  一种电解质组成物，其耐久性和电荷传输性能优异，以及一种电化学电池，其中时间内电荷传输性能的恶化被最小化，该电解质组成物包括一种盐，其包含一种含有介质基团的阴离子，并且在阴离子的结构中具有6个或更多碳的烷基或烯基基团，以及一种有机或无机阳离子。
• DRUGS INHIBITING CELL DEATH
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP1224932A1

  公开（公告）日：2002-07-24

  A cell death inhibitor, a pharmaceutical or a preservative for organs, tissues or cells, a comprising, as an active ingredient, an indolylmaleimide derivative represented by the following formula (I), which is useful for inhibiting death of cells, the drug being expected as a preventive or a remedy for the progress of various diseases wherein cell death participates in progress and exacerbation thereof:

  一种细胞死亡抑制剂，一种用于器官、组织或细胞的药物或防腐剂，其有效成分包括由下式（I）代表的吲哚马来酰亚胺衍生物，该衍生物可用于抑制细胞死亡，该药物可望作为各种疾病的预防或治疗药物，在这些疾病中，细胞死亡参与了疾病的进展和恶化：
• 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.
• Development of a Water-Soluble Indolylmaleimide Derivative IM-93 Showing Dual Inhibition of Ferroptosis and NETosis
  作者：Kosuke Dodo、Erika Kuboki、Tadashi Shimizu、Ryu Imamura、Megumi Magarisawa、Masahiro Takahashi、Takuto Tokuhiro、Satoshi Yotsumoto、Kenichi Asano、Shuhei Nakao、Naoki Terayama、Takashi Suda、Masato Tanaka、Mikiko Sodeoka

  DOI：10.1021/acsmedchemlett.9b00142

  日期：2019.9.12

  The indolylmaleimide (IM) derivative IM-17 shows inhibitory activity against oxidative-stress-induced necrotic cell death and cardioprotective activity in rat ischemia-reperfusion injury models. In order to develop a more potent derivative, we conducted a detailed structure-activity relationship study of IM derivatives and identified IM 93 as the most potent derivative with good water solubility. IM-93 inhibited ferroptosis and NETosis, but not necroptosis or pyroptosis. In contrast, ferrostatin-1 (Fer-1), a ferroptosis inhibitor, did not inhibit NETosis, although the accompanying lipid peroxidation was partially inhibited by Fer-1, as well as by IM-93. Thus, IM derivatives have a unique activity profile and appear to be promising candidates for in vivo application.
• 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.