1-Methylindirubin | 85144-53-2

• 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-Methylindirubin
• 英文别名: (Z)-1'-methyl-1H,1'H-[2,3']biindolylidene-3,2'-dione；(Z)-1'-Methyl-1H,1'H-[2,3']biindolyliden-3,2'-dion；(3Z)-1-methyl-3-(3-oxo-1H-indol-2-ylidene)indol-2-one
• CAS: 85144-53-2
• 化学式: C₁₇H₁₂N₂O₂
• 分子量: 276.294
• InChiKey: WDRLURVRNVIUKR-PFONDFGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  21.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-Methylindirubin 在 吡啶 、 盐酸羟胺 作用下， 以77 %的产率得到1-Methylindirubin-3'-oxime
  参考文献：
  名称：

  The role of the oxime group in the excited state deactivation processes of indirubin

  摘要：

  利用快速瞬态吸收和发射（fs-TA/fs-UC）以及稳态荧光技术，探讨了在靛蓝（INR）衍生物（INROx、MINROx、6-BrINROx）中添加肟基对其光谱和光物理特性的影响。

  DOI：

  10.1039/d3cp05260e
• 作为产物：
  描述：

  靛红 在 sodium hydride 、 sodium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 1-Methylindirubin
  参考文献：
  名称：

  Synthesis of novel 5-substituted indirubins as protein kinases inhibitors

  摘要：

  In an effort to identify new pharmacological inhibitors of disease-relevant protein kinases with increased potency and selectivity, we synthesized and evaluated new 5-substituted indirubins. The effects of 34 indirubin derivatives on CDK1/cyclin B, CDK5/p25, and GSK-3, as well as on SH-SY5Y human neuroblastoma cell survival, were investigated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.036

文献信息

• Structural Basis for the Synthesis of Indirubins as Potent and Selective Inhibitors of Glycogen Synthase Kinase-3 and Cyclin-Dependent Kinases
  作者：Panagiotis Polychronopoulos、Prokopios Magiatis、Alexios-Leandros Skaltsounis、Vassilios Myrianthopoulos、Emmanuel Mikros、Aldo Tarricone、Andrea Musacchio、S. Mark Roe、Laurence Pearl、Maryse Leost、Paul Greengard、Laurent Meijer

  DOI：10.1021/jm031016d

  日期：2004.2.1

  Pharmacological inhibitors of glycogen synthase kinase-3 (GSK-3) and cyclin-dependent kinases have a promising potential for applications against several neurodegenerative diseases such as Alzheimer's disease. Indirubins, a family of bis-indoles isolated from various natural sources, are potent inhibitors of several kinases, including GSK-3. Using the cocrystal structures of various indirubins with GSK-3beta, CDK2 and CDK5/p25, we have modeled the binding of indirubins within the ATP-binding pocket of these kinases. This modeling approach provided some insight into the molecular basis of indirubins' action and selectivity and allowed us to forecast some improvements of this family of bis-indoles as kinase inhibitors. Predicted molecules, including 6-substituted and 5,6-disubstituted indirubins, were synthesized and evaluated as CDK and GSK-3 inhibitors. Control, kinase-inactive indirubins were obtained by introduction of a methyl substitution on N1.
• Porter et al., Journal of the Chemical Society, 1941, p. 620,621
  作者：Porter et al.

  DOI：——

  日期：——
• Synthesis of novel 5-substituted indirubins as protein kinases inhibitors
  作者：A BEAUCHARD、Y FERANDIN、S FRERE、O LOZACH、M BLAIRVACQ、L MEIJER、V THIERY、T BESSON

  DOI：10.1016/j.bmc.2006.05.036

  日期：2006.9.15

  In an effort to identify new pharmacological inhibitors of disease-relevant protein kinases with increased potency and selectivity, we synthesized and evaluated new 5-substituted indirubins. The effects of 34 indirubin derivatives on CDK1/cyclin B, CDK5/p25, and GSK-3, as well as on SH-SY5Y human neuroblastoma cell survival, were investigated. (c) 2006 Elsevier Ltd. All rights reserved.
• The role of the oxime group in the excited state deactivation processes of indirubin
  作者：Danîela C. Nobre、Estefanía Delgado-Pinar、Carla Cunha、J. Sérgio Seixas de Melo

  DOI：10.1039/d3cp05260e

  日期：——

  The impact of adding an oxime group to indirubin (INR) derivatives (INROx, MINROx, 6-BrINROx) on their spectral and photophysical properties was explored using fast-transient absorption and emission (fs-TA/fs-UC) and steady-state fluorescence techniques.

  利用快速瞬态吸收和发射（fs-TA/fs-UC）以及稳态荧光技术，探讨了在靛蓝（INR）衍生物（INROx、MINROx、6-BrINROx）中添加肟基对其光谱和光物理特性的影响。