2,3-bis-(7-methyl-1H-indol-3-yl)-N-methylmaleimide | 152537-94-5

• 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: 2,3-bis-(7-methyl-1H-indol-3-yl)-N-methylmaleimide
• 英文别名: 1-methyl-3,4-bis(7-methyl-1H-indol-3-yl)pyrrole-2,5-dione
• CAS: 152537-94-5
• 化学式: C₂₃H₁₉N₃O₂
• 分子量: 369.423
• InChiKey: OSLZJFUPSYYPPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  69
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-bis-(7-methyl-1H-indol-3-yl)-N-methylmaleimide 在 乙酸铵 、 氢氧化钾 作用下， 以 1,4-二氧六环 为溶剂， 生成 2,3-bis-(7-methyl-1H-indol-3-yl)-maleimide
  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
• 作为产物：
  描述：

  7-甲基吲哚 、 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30%的产率得到2,3-bis-(7-methyl-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-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.
• INDOLE DERIVATIVES WITH ANTIVIRAL ACTIVITY
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0630241A1

  公开（公告）日：1994-12-28
• US6589977B1
  申请人：——

  公开号：US6589977B1

  公开（公告）日：2003-07-08