3-(1-methyl-1H-indol-3-yl)-4-phenyl-1H-pyrrole-2,5-dione | 125313-97-5

• 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-(1-methyl-1H-indol-3-yl)-4-phenyl-1H-pyrrole-2,5-dione
• 英文别名: 3-(1-methyl-3-indolyl)-4-phenyl-1H-pyrrole-2,5-dione；2-(1-methyl-1H-indol-3-yl)-3-phenylmaleimide；(Arylindolyl)maleimide deriv. 23；3-(1-methylindol-3-yl)-4-phenylpyrrole-2,5-dione
• CAS: 125313-97-5
• 化学式: C₁₉H₁₄N₂O₂
• 分子量: 302.332
• InChiKey: AXRADSPPGKCCQJ-UHFFFAOYSA-N

物化性质

• 熔点：
  256-257 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  556.0±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  51.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1-methyl-1H-indol-3-yl)-4-phenyl-1H-pyrrole-2,5-dione 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以97%的产率得到2-(1-methyl-1H-indol-3-yl)-3-phenyl-N-methylmaleimide
  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：

  1-methylindole-3-glyoxylyl chloride 在 ammonium hydroxide 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 3-(1-methyl-1H-indol-3-yl)-4-phenyl-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  A Practical Method for the Synthesis of Indolylaryl- and Bisindolylmaleimides

  摘要：

  Indolylaryl and indolylheteroarylmaleimides, including bisindolylmaleimides, are easily prepared by the reaction of N-methylindole-3-glyoxylamide with methyl aryl acetates in the presence of potassium tert-butoxide in THF.

  DOI：

  10.1021/ol0621203

文献信息

• A new one step synthesis of maleimides by condensation of glyoxylate esters with acetamides
  作者：Margaret M. Faul、Leonard L. Winneroski、Christine A. Krumrich

  DOI：10.1016/s0040-4039(98)02594-5

  日期：1999.2

  Bisphenyl, Bisheteroaryl, indolylaryl and indolylcycloalkyl maleimides are prepared in one step and 67–99% yield by condensation of glyoxylate esters with acetamides using a 1.0 M solution of potassium tert-butoxide in THF. The mechanism of the reaction is discussed.

  使用1.0 M叔丁醇钾的THF溶液，通过乙醛酸酯与乙酰胺的缩合，可一步制备联苯，二异芳基，吲哚基芳基和吲哚基环烷基马来酰亚胺，收率67-99％。讨论了反应机理。
• Process for the preparation of 2-substituted and 2,3-disubstituted
  申请人：Hoffmann-La Roche Inc.

  公开号：US05399712A1

  公开（公告）日：1995-03-21

  The invention relates to a process for the manufacture of substituted maleimides of the formula ##STR1## wherein R.sup.1 is alkyl, aryl or heteroaryl and R.sup.2 is hydrogen, alkyl, alkoxycarbonyl, aryl or heteroaryl, by reacting an activated glyoxylate of the formula ##STR2## wherein R.sup.1 has the above significance and X is a leaving atom or group, with an imidate of the formula ##STR3## wherein R.sup.2 has the above significance, R.sup.3 is alkyl, aryl or trialkylsilyl and Y is oxygen or sulfur, in the presence of a base and, after treating the resulting reaction product obtained in which R.sup.2 is hydrogen or alkyl with a strong base, hydrolyzing and dehydrating the resulting hydroxy-pyrrolinone of the formula ##STR4## wherein R.sup.1, R.sup.2, R.sup.3 and Y have the above significance. The substituted maleimides of formula I are pharmacologically active, for example as protein kinase C inhibitors and which a useful, for example, in the treatment and prophylaxis of inflammatory, immunological, bronchopulmonary and cardiovascular disorders, or as antiproliferative agents useful, for example, in the treatment of immune diseases and allergic disorders.

  该发明涉及一种制备式为##STR1##的取代马来酰亚胺的方法，其中R.sup.1是烷基、芳基或杂环芳基，R.sup.2是氢、烷基、烷氧羰基、芳基或杂环芳基，通过将式为##STR2##的活化的甘醇酸酯与式为##STR3##的亚胺在碱存在下反应，其中R.sup.1具有上述含义，X是一个脱离原子或基团，然后处理所得的反应产物，其中R.sup.2是氢或烷基，用强碱处理后，水解和脱水所得的式为##STR4##的羟基吡咯烷酮，其中R.sup.1、R.sup.2、R.sup.3和Y具有上述含义。式I的取代马来酰亚胺在药理学上具有活性，例如作为蛋白激酶C抑制剂，可用于治疗和预防炎症、免疫、支气管肺部和心血管疾病，或作为抗增殖剂，例如用于治疗免疫性疾病和过敏性疾病。
• Indolylpyrrole derivatives and cell death inhibitors
  申请人：——

  公开号：US20030087949A1

  公开（公告）日：2003-05-08

  The invention provides a compound represented by the following formula (I) 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: 1 and, a cell death inhibitor, a drug or a preservative for cells, organs or tissues or cells, each comprising the derivative as an active ingredient.

  本发明提供了一种化合物，其化学式表示为(I)，可用于抑制细胞死亡。该药物预期可作为预防或治疗各种细胞死亡参与病程和恶化的疾病的药物，同时还提供了一种细胞死亡抑制剂、细胞、器官或组织的药物或保护剂，每种药物均包含该衍生物作为活性成分。
• Substituierte Pyrrole
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0328026A1

  公开（公告）日：1989-08-16

  Pyrrole der allgemeinen Formel worin R¹, R², R³, R⁴, R⁵, R⁶, R⁷, X und Y die in der Beschreibung angegebene Bedeutung haben sind verwendbar bei der Behandlung oder Prophylaxe von inflammatorischen, immunologischen, bronchopulmonären oder cardiovaskulären Krankheiten. Sie werden ausgehend von entsprechend substituierten Furanen oder von auf andere Weise substituierten Pyrrolen hergestellt.

  通式如下的吡咯 其中 R¹、R²、R³、R⁴、R⁵、R⁶、R⁷、X 和 Y 具有说明中给出的含义，可用于治疗或预防炎症、免疫学、支气管肺病或心血管疾病。 它们由适当取代的呋喃或其他取代的吡咯制备而成。
• INDOLYLPYRROLE DERIVATIVES AND CELL DEATH INHIBITORS
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP1275646A1

  公开（公告）日：2003-01-15

  The invention provides a compound represented by the following formula (I) 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: and, a cell death inhibitor, a drug or a preservative for cells, organs or tissues or cells, each comprising the derivative as an active ingredient.

  本发明提供了一种由下式(I)代表的化合物，该化合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： 以及细胞死亡抑制剂、细胞、器官或组织或细胞的药物或防腐剂，每一种都包含该衍生物作为活性成分。