6-aminoindoline-2,3-dione | 116081-74-4

• 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: 6-aminoindoline-2,3-dione
• 英文别名: 6-Amino-indolin-2,3-dion；6-amino-1H-indole-2,3-dione
• CAS: 116081-74-4
• 化学式: C₈H₆N₂O₂
• mdl: MFCD01548336
• 分子量: 162.148
• InChiKey: NAZUFMFAUQMVSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-aminoindoline-2,3-dione 、 吲哚乙酸酯 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以57%的产率得到(2'Z)-6-aminoindirubin
  参考文献：
  名称：

  Synthesis and kinase inhibitory activity of novel substituted indigoids

  摘要：

  The bis-indole indigoids are a promising protein kinase inhibitor scaffold to be further evaluated against the numerous human diseases that imply abnormal regulation of kinases including neurodegenerative disorders. In an effort to identify new pharmacological inhibitors of disease-relevant protein kinases with increased potency and selectivity, we designed, synthesized new 5,7-disubstituted or 6-substituted bis-indole derivatives. On the basis of our previous synthetic work, 22 selected compounds were tested on CDK1/cyclin B, CDK5/p25, DYRK1A, CK1, and GSK-3 alpha/beta kinases, five kinases involved in Alzheimer's disease. Some of them were also evaluated for their cytotoxic and antiproliferative activities. 6-Nitro-3'-N-oxime-indirubin and 5-amino-3'- N-oxime-indirubin derivatives exhibited inhibitory activity in a submicromolar range against CDK1/cyclin B (0.18 and 0.1 mu M, respectively), CK1 (0.6 mu M and 0.13 mu M) and GSK3 (0.04 mu M and 0.36 mu M). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.051
• 作为产物：
  描述：

  2,4-diamino-1-iodobenzene 在 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 35.0h， 生成 6-aminoindoline-2,3-dione
  参考文献：
  名称：

  钯催化双羰基化方法从 2-碘苯胺制备靛红

  摘要：

  已开发出合成靛红的高产程序。用接近化学计量的 CO 对 2-碘苯胺进行连续 Pd 催化双羰基化，然后进行酸促进环化，很容易得到一系列靛红。发现 2-碘苯胺以良好到极好的产率转化为靛红，具有良好的官能团耐受性。该协议证明适用于靛红的 13C 同位素标记, 并扩展到 13C 同位素标记的抗病毒药物美替沙宗和实验性抗精神分裂症药物 ML137 的合成。

  DOI：

  10.1002/ejoc.201600143

文献信息

• Structure-based design and parallel synthesis of N-benzyl isatin oximes as JNK3 MAP kinase inhibitors
  作者：Jingrong Cao、Huai Gao、Guy Bemis、Francesco Salituro、Mark Ledeboer、Edmund Harrington、Susanne Wilke、Paul Taslimi、S. Pazhanisamy、Xiaoling Xie、Marc Jacobs、Jeremy Green

  DOI：10.1016/j.bmcl.2009.03.043

  日期：2009.5

  A series of N-benzylated isatin oximes were developed as inhibitors of the mitogen-activated kinase, JNK3. X-ray crystallographic structures aided in the design and synthesis of novel, selective compounds, that inhibit JNK3, but not p38 MAP kinase and provided key insights into understanding the behavior of gatekeeper residue methionine-146 in determining target selectivity for this series.
• Synthesis and kinase inhibitory activity of novel substituted indigoids
  作者：Anne Beauchard、Hélène Laborie、Hervé Rouillard、Olivier Lozach、Yoan Ferandin、Rémy Le Guével、Christiane Guguen-Guillouzo、Laurent Meijer、Thierry Besson、Valérie Thiéry

  DOI：10.1016/j.bmc.2009.07.051

  日期：2009.9.1

  The bis-indole indigoids are a promising protein kinase inhibitor scaffold to be further evaluated against the numerous human diseases that imply abnormal regulation of kinases including neurodegenerative disorders. In an effort to identify new pharmacological inhibitors of disease-relevant protein kinases with increased potency and selectivity, we designed, synthesized new 5,7-disubstituted or 6-substituted bis-indole derivatives. On the basis of our previous synthetic work, 22 selected compounds were tested on CDK1/cyclin B, CDK5/p25, DYRK1A, CK1, and GSK-3 alpha/beta kinases, five kinases involved in Alzheimer's disease. Some of them were also evaluated for their cytotoxic and antiproliferative activities. 6-Nitro-3'-N-oxime-indirubin and 5-amino-3'- N-oxime-indirubin derivatives exhibited inhibitory activity in a submicromolar range against CDK1/cyclin B (0.18 and 0.1 mu M, respectively), CK1 (0.6 mu M and 0.13 mu M) and GSK3 (0.04 mu M and 0.36 mu M). (C) 2009 Elsevier Ltd. All rights reserved.
• A Palladium-Catalyzed Double Carbonylation Approach to Isatins from 2-Iodoanilines
  作者：Simon R. Laursen、Mikkel T. Jensen、Anders T. Lindhardt、Mikkel F. Jacobsen、Troels Skrydstrup

  DOI：10.1002/ejoc.201600143

  日期：2016.4

  A high-yielding procedure for the synthesis of isatins has been developed. Sequential Pd-catalyzed double carbonylation of 2-iodoanilines with near stoichiometric amounts of CO followed by acid-promoted cyclization readily affords an array of isatins. The conversion of 2-iodoanilines to isatins in good to excellent yields was found to proceed with good functional group tolerance. This protocol proved

  已开发出合成靛红的高产程序。用接近化学计量的 CO 对 2-碘苯胺进行连续 Pd 催化双羰基化，然后进行酸促进环化，很容易得到一系列靛红。发现 2-碘苯胺以良好到极好的产率转化为靛红，具有良好的官能团耐受性。该协议证明适用于靛红的 13C 同位素标记, 并扩展到 13C 同位素标记的抗病毒药物美替沙宗和实验性抗精神分裂症药物 ML137 的合成。