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

• 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: 1-methyl-3-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione
• 英文别名: 1-Methyl-3-(1-methylindol-3-yl)pyrrole-2,5-dione；1-methyl-3-(1-methylindol-3-yl)pyrrole-2,5-dione
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: PFADLRMJVSJAGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  1-methyl-3-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以75%的产率得到3-iodo-1-methyl-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  碘促进马来酰亚胺与二甲基亚砜和硫醇的C（sp2）–H硫醇化

  摘要：

  §谭红如和王纶对这项工作做出了同样的贡献。 抽象的 已经开发了使用DMSO作为合成子的碘促进马来酰亚胺的C（sp 2）–H甲基硫醇化反应，可以在无金属条件下以中等收率得到3-甲基硫代马来酰亚胺。另外，在碘和三乙胺的存在下，由马来酰亚胺和硫醇合成了3-硫代马来酰亚胺。该方法对于形成C–S键很简单有效。 已经开发了使用DMSO作为合成子的碘促进马来酰亚胺的C（sp 2）–H甲基硫醇化反应，可以在无金属条件下以中等收率得到3-甲基硫代马来酰亚胺。另外，在碘和三乙胺的存在下，由马来酰亚胺和硫醇合成了3-硫代马来酰亚胺。该方法对于形成C–S键很简单有效。

  DOI：

  10.1055/s-0037-1609585
• 作为产物：
  描述：

  3-(1H-indol-3-yl)-1-methylpyrrolidine-2,5-dione 在 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-methyl-3-(1-methyl-1H-indol-3-yl)-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

• Cu/Ag-Cocatalyzed Aerobic Oxidative Amination and CuCl₂-Mediated Aerobic Oxidative Chloroamination of Maleimides
  作者：Yu-Long An、He-Hui Zhang、Zhen-Hua Yang、Long Lin、Sheng-Yin Zhao

  DOI：10.1002/ejoc.201600923

  日期：2016.11

  An efficient Cu(OAc)2/Ag2CO3-cocatalyzed approach for the synthesis of 3-aminomaleimides and 3-amino-4-indolylmaleimides has been developed with satisfactory yields. A series of primary and secondary amines are compatible with this reaction. In addition, treatment of maleimides with primary amines using 1 equiv. of CuCl2 leads to the formation of chloroamination products such as 3-amino-4-chloromaleimides

  已开发出一种有效的 Cu(OAc)2/Ag2CO3 共催化方法来合成 3-氨基马来酰亚胺和 3-氨基-4-吲哚基马来酰亚胺，收率令人满意。一系列伯胺和仲胺与该反应相容。此外，使用 1 当量的伯胺处理马来酰亚胺。CuCl2 通过自由基型机制导致氯胺化产物如 3-氨基-4-氯马来酰亚胺的形成。
• Convenient construction of spiro[indoline-3,5'-pyrrolo[3,4-c]carbazole] and spiro[indene-2,5'-pyrrolo[3,4-c]carbazole] via acid-catalyzed Diels-Alder reaction
  作者：Chen Yan、Jing Sun、Chao-Guo Yan

  DOI：10.1016/j.cclet.2020.08.052

  日期：2021.3

  p-TsOH catalyzed Diels-Alder reaction of 3-(indol-3-yl)maleimides with 3-phenacylideneoxindoles in toluene at 80 °C for two hours afforded cis/trans isomers of 3a',4′,6′,10c'-tetrahydrospiro[indoline-3,5′-pyrrolo[3,4-c]carbazoles] in nearly comparable yields, which could be easily converted to the corresponding 4′,6′-dihydrospiro[indoline-3,5′-pyrrolo[3,4-c]carbazole] in high yields and with high

  p-TsOH在甲苯中于80°C催化3-（吲哚-3-基）马来酰亚胺与3-苯甲叉基氧吲哚的Diels-Alder反应2小时，得到3a'，4'，6'，10c'-的顺式/反式异构体四氢螺[吲哚啉-3,5'-吡咯并[3,4-c]咔唑]的收率几乎相当，可以轻松转化为相应的4'，6'-二氢螺[吲哚啉-3,5'-吡咯并[3] ，4- c ]咔唑]通过进一步的DDQ氧化以高收率和高非对映选择性形成。此外，3-（吲哚-3-基）马来酰亚胺与2-亚芳基-1,3-茚二酮在甲苯中80°C的相似反应和顺序DDQ氧化得到官能化的二氢螺[indene-2,5'-pyrrolo [3， 4- c ]咔唑]为主要产品。
• Direct Synthesis of Fused Thienoindoles via Base Promoted Double C−H Sulfuration with Elemental Sulfur
  作者：Shanping Chen、Kai Hu、Wei Feng、Guojiang Mao、Yuxia Li、Guo‐Jun Deng

  DOI：10.1002/adsc.202300443

  日期：2023.6.13

  indoles and elemental sulfur has been reported. The present approach produces a range of structurally valuable fused thienoindoles in 51–78% yield under transition-metal-free conditions, which may have potential applications in pharmaceutical industry and organic functional materials. In this work, the double C−S bonds formation is achieved via base promoted direct sulfuration of C−H bonds with elemental

  已经报道了从取代的吲哚和元素硫制备稠合噻吩并吲哚的直接策略。本方法在无过渡金属条件下以 51-78% 的产率生产一系列具有结构价值的稠合噻吩并吲哚，这可能在制药工业和有机功能材料中具有潜在的应用。在这项工作中，双 C-S 键的形成是通过碱促进 C-H 键与元素硫的直接硫化来实现的。
• Selective construction of polycyclic cyclohepta[<i>b</i>]indoles and cyclopenta[<i>b</i>]indoles <i>via</i> cycloaddition reaction of 3-(indol-3-yl)maleimides and (indol-2-yl)methanols
  作者：Jing Sun、Chen Yan、Qiu Sun、Ying Han、Chao-Guo Yan

  DOI：10.1039/d3nj00013c

  日期：——

  annulation reaction of 3-(indol-3-yl)maleimides and (indol-2-yl)diphenylmethanols in chloroform afforded functionalized pyrrolo[3′,4′:6,7]cyclohepta[1,2-b:4,5-b′]diindoles in satisfactory yields, in which a formal [4+3] cycloaddition and an unprecedented rearrangement of the maleimide motif from the C3- to C2-position of the indole ring was firstly observed. Alternatively, the similar reaction of 3-(i

  p -TsOH 促进 3-(indol-3-yl) 马来酰亚胺和 (indol-2-yl) 二苯基甲醇在氯仿中的环化反应，得到功能化的吡咯并[3',4':6,7]环庚[1,2- b ]： 4,5- b ']二吲哚的产率令人满意，其中首次观察到正式的 [4+3] 环加成和马来酰亚胺基序从吲哚环的 C3 位到 C2 位的前所未有的重排。或者，3-(indol-3-yl) 马来酰亚胺和 3-hydroxy-3-(indol-3-yl)-indolin-2-ones 在乙腈中的类似反应得到官能化的螺 [indoline-3,9'-pyrrolo [3',4':4,5]cyclopenta[1,2- b ]indole] 产率高，非对映选择性高。另一方面，p-TsOH 促进 3-(indol-3-yl) 马来酰亚胺和 2-hydroxy-2-(indol-3-yl)-indene-1,3-diones
• 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.