2,3-bis-(5-methoxy-1H-indol-3-yl)-N-methylmaleimide | 137108-30-6

• 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: 2,3-bis-(5-methoxy-1H-indol-3-yl)-N-methylmaleimide
• 英文别名: 2,3-bis(5-methoxy-1H-indol-3-yl)-N-methylmaleimide；3,4-bis(5-methoxy-1H-indol-3-yl)-1-methylpyrrole-2,5-dione
• CAS: 137108-30-6
• 化学式: C₂₃H₁₉N₃O₄
• 分子量: 401.422
• InChiKey: IRUNJAFIQSAZDE-UHFFFAOYSA-N

物化性质

• 熔点：
  >260 °C
• 沸点：
  700.6±60.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  87.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-bis-(5-methoxy-1H-indol-3-yl)-N-methylmaleimide 在 palladium-carbon 氢气 、 palladium-carbon 、 silica gel 、 乙酸乙酯 、 正己烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以to obtain 3,4-bis(5-methoxy-1H-indol-3-yl)-1-methyl-2,5-dioxopyrrolidine (20 mg, 19.9%)的产率得到3,4-bis(5-methoxy-1H-indol-3-yl)-1-methyl-2,5-dioxopyrrolidine
  参考文献：
  名称：

  Pyrrole derivatives and cell death inhibitors

  摘要：

  一般式为I的双吲哚基吡咯衍生物，在抑制细胞死亡方面非常有用，预计可作为预防和治疗参与细胞死亡的各种疾病的药物，以及含有这些衍生物或其药学上可接受的盐为活性成分的细胞死亡抑制剂、药物和细胞/组织/器官保护剂。

  公开号：

  US06589977B1
• 作为产物：
  描述：

  5-甲氧基吲哚 、 2,3-二氯-N-甲基马来酰亚胺顺丁烯二酰亚胺 在 乙基溴化镁 作用下， 以 四氢呋喃 、 苯 为溶剂， 以36%的产率得到2,3-bis-(5-methoxy-1H-indol-3-yl)-N-methylmaleimide
  参考文献：
  名称：

  Indolocarbazoles: potent, selective inhibitors of human cytomegalovirus replication

  摘要：

  In our search for new, safer anti-HCMV agents, we discovered that the natural product Arcyriaflavin A (la) was a potent inhibitor of HCMV replication in cell culture. A series of analogues (symmetrical indolocarbazoles) was synthesised to investigate structure-activity relationships in this series against a range of herpes viruses (HCMV, VZV, HSV1, and 2). This identified a number of novel, selective and potent inhibitors of HCMV, 12,13-dihydro-2,10-difluoro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(6H)-dione (Id) being the best example (IC50 = 40 nM, therapeutic index > 1450). Compounds described in this series were generally poor inhibitors of protein kinase C beta II, and no correlation was found between the ability to inhibit HCMV and the enzyme PKC. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00032-2

文献信息

• Synthesis of Indolo[2,3-<i>a</i>]pyrrolo[3,4-<i>c</i>]carbazoles by Oxidative Cyclization of Bisindolylmaleimides with a Rhodium(III)-Copper(II) Catalytic System
  作者：Bernhard Witulski、Torsten Schweikert

  DOI：10.1055/s-2005-869977

  日期：——

  A novel catalytic protocol for the synthesis of a series of indolo[2,3-a]pyrrolo[3,4-c]carbazoles based on the bimetallic system RhCl 3 .3H 2 O and Cu(OAc) 2 .H 2 O in the presence of molecular oxygen was investigated. The method was applied to the synthesis of the glycosidated fluoroindolocarbazole 3 that was recently isolated as a metabolite from feeding experiments of Saccharothrix aerocolonigenes

  基于双金属体系 RhCl 3 .3H 2 O 和 Cu(OAc) 2 .H 2 O 合成一系列吲哚[2,3-a]吡咯并[3,4-c]咔唑的新催化方案研究了分子氧的存在。该方法应用于糖苷化的氟吲哚咔唑 3 的合成，该糖苷化的氟吲哚咔唑 3 最近作为一种代谢物从产气结肠糖丝菌 ATCC 39243 与氟色氨酸的喂养实验中分离出来。
• Synthesis of Indolo[2,3-a]pyrrolo[3,4-c]carbazoles via the Oxidative Cyclization of Bisindolylmaleimides with Pd(TFA)₂/Cu(OAc)₂
  作者：Xuan Pan、Ke Wang、Bao He Guan、Zhan Zhu Liu

  DOI：10.1002/jhet.2134

  日期：2015.5

  A new synthetic approach for the synthesis of indolo[2,3‐a]pyrrolo[3,4‐c]carbazoles based on the Cu2+/Pd2+ catalytic system is described. The optimum condition is established via a systematic screening and utilized for the synthesis of four indolocarbazole aglycones with a satisfied yield.

  描述了一种基于Cu 2+ / Pd 2+催化体系合成吲哚[2,3-a]吡咯并[3,4-c]咔唑的新方法。通过系统的筛选确定了最佳条件，并以令人满意的产率用于合成四种吲哚并咔唑糖苷配基。
• PYRROLE DERIVATIVES AND CELL DEATH INHIBITORS
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP1152002A1

  公开（公告）日：2001-11-07

  Bisindolylpyrrole derivatives represented by general formula [I] which are useful in inhibiting cell death and expected as being useful as preventives and remedies for the progress of various diseases in the progress and worsening of which cell death participates; and cell death inhibitors, drugs and cell/tissue/organ preservatives containing as the active ingredient these derivatives or pharmaceutically acceptable salts thereof.

  由通式[I]表示的双吲哚基吡咯衍生物，可用于抑制细胞死亡，并可望作为预防和治疗细胞死亡导致的各种疾病的进展和恶化的药物；以及含有这些衍生物或其药学上可接受的盐类作为活性成分的细胞死亡抑制剂、药物和细胞/组织/器官防腐剂。
• Structure–activity relationship of N-methyl-bisindolylmaleimide derivatives as cell death inhibitors
  作者：Miho Katoh、Kosuke Dodo、Mikako Fujita、Mikiko Sodeoka

  DOI：10.1016/j.bmcl.2005.04.015

  日期：2005.6

  A series of N-methyl-bisindolylmaleimide derivatives was synthesized and evaluated as cell death inhibitors. N-Methyl-2[1-(3-aminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)maleimide (21) was the most potent inhibitor of H2O2-induced necrotic death of human leukemia HL60 cells among them. (c) 2005 Elsevier Ltd. All rights reserved.
• US6589977B1
  申请人：——

  公开号：US6589977B1

  公开（公告）日：2003-07-08