5-Aminoindirubin | 910035-26-6

• 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: 5-Aminoindirubin
• 英文别名: (Z)-5'-amino-[2,3'-biindolinylidene]-2',3-dione；5'-amino-1H,1'H-[2,3']biindolylidene-3,2'-dione；5-amino-indirubin；(3Z)-5-amino-3-(3-oxo-1H-indol-2-ylidene)-1H-indol-2-one
• CAS: 910035-26-6
• 化学式: C₁₆H₁₁N₃O₂
• 分子量: 277.282
• InChiKey: UKVQMBJHWHGXOI-YPKPFQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 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：
  0.0
• 拓扑面积：
  84.22
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-Aminoindirubin 以 吡啶 为溶剂， 以64%的产率得到5-Acetylaminoindirubin
  参考文献：
  名称：

  Indigoid bisindole derivatives

  摘要：

  本发明涉及一种新型吲哚蓝类二氮烷衍生物，可用于制造用于治疗实体癌症的药物。

  公开号：

  US06987092B1
• 作为产物：
  描述：

  吲哚乙酸酯 在 铁粉 、 sodium carbonate 、 氯化铵 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 5-Aminoindirubin
  参考文献：
  名称：

  通过高通量筛选发现靛玉红衍生物作为新型DRAK2抑制剂

  摘要：

  DRAK2是属于死亡相关蛋白激酶（DAPK）家族的丝氨酸/苏氨酸激酶，已经成为治疗自身免疫性疾病和癌症的有希望的药物靶标。为了鉴定DRAK2的小分子抑制剂，我们使用内部化学文库进行了高通量筛选活动，并将靛玉红3'-一氧化二铁鉴定为新型的DRAK2抑制剂。在测试的化合物中，化合物16对DRAK2表现出最强的抑制活性（IC 50  = 0.003μM ）。我们还提出，基于酶动力学和分子对接研究，化合物16可与酶的ATP结合位点结合。

  DOI：

  10.1016/j.bmcl.2016.03.111

文献信息

• [EN] INDIRUBIN-TYPE COMPOUNDS, COMPOSITIONS, AND METHODS FOR THEIR USE<br/>[FR] COMPOSES DE TYPE INDIRUBINE, COMPOSITIONS ET LEURS PROCEDES D'UTILISATION
  申请人：UNIV ROCKEFELLER

  公开号：WO2005041954A1

  公开（公告）日：2005-05-12

  Compounds and compositions including 6-bromo-indirubin, 5-amino-indirubin and N-methyl-indirubins and related indirubin derivatives are provided that are useful as selective modulators of glycogen synthase kinase-3, cyclin-dependent protein kinases or aryl hydrocarbon receptors. Methods of inhibiting or modulating cell growth or cell cycling are provided using the compounds of the invention. In other aspects, compounds and methods for the treatment of protozoan-mediated diseases, Alzheimer's disease and diabetes are provided.

  提供了包括6-溴吲哚红、5-氨基吲哚红和N-甲基吲哚红以及相关吲哚红衍生物的化合物和组合物，这些化合物对于选择性调节糖原合酶激酶-3、细胞周期蛋白激酶或芳香烃受体非常有用。利用本发明的化合物提供了抑制或调节细胞生长或细胞周期的方法。在其他方面，提供了用于治疗原虫介导疾病、阿尔茨海默病和糖尿病的化合物和方法。
• [EN] INDIRUBIN DERIVATIVES HAVING ANTICANCER PROPERTY AGAINST HUMAN CANCER CELL ME<br/>[FR] DERIVES D'INDIRUBINE POSSEDANT UNE PROPRIETE ANTI-CANCER CONTRE LA LIGNEE CELLULAIRE DU CANCER HUMAIN
  申请人：ANYGEN CO LTD

  公开号：WO2005070416A1

  公开（公告）日：2005-08-04

  The present invention relates to an indirubin derivative having anticancer property by inhibiting cell proliferation as to human cancer cell line. More particularly, this invention provides the synthesis of indirubin derivative known as CDK(Cyclin-dependent kinase) inhibitor. Further, inhibition activity of proliferation as to human cancer cell line and apoptosis against induced-differentiation of said indirubin derivative are researched to develop a novel indirubin derivative having efficacious anticancer properties as to various human cell lines.

  本发明涉及一种通过抑制细胞增殖具有抗癌性能的靛蓝衍生物，针对人类癌细胞系。更具体地，该发明提供了一种被称为CDK（细胞周期依赖性激酶）抑制剂的靛蓝衍生物的合成。此外，针对人类癌细胞系的增殖抑制活性和对所述靛蓝衍生物诱导分化的细胞凋亡进行了研究，以开发一种具有有效抗癌性能的新型靛蓝衍生物，适用于各种人类细胞系。
• Indirubin-Type Compounds, Compositions, and Methods for Their Use
  申请人：Meijer Laurent

  公开号：US20070276025A1

  公开（公告）日：2007-11-29

  Compounds and compositions including 6-bromo-indirubin, 5-amino-indirubin and N-methyl-indirubins and related indirubin derivatives are provided that are useful as selective modulators of glycogen synthase kinase-3, cyclin-dependent protein kinases or aryl hydrocarbon receptors. Methods of inhibiting or modulating cell growth or cell cycling are provided using the compounds of the invention. In other aspects, compounds and methods for the treatment of protozoan-mediated diseases, Alzheimer's disease and diabetes are provided.

  提供了包括6-溴吲哚红、5-氨基吲哚红和N-甲基吲哚红及相关吲哚红衍生物的化合物和组合物，它们可用作选择性调节糖原合酶激酶-3、周期蛋白依赖性蛋白激酶或芳香族羟基化酶的调节剂。使用本发明的化合物提供了抑制或调节细胞生长或细胞周期的方法。在其他方面，提供了治疗原虫介导疾病、阿尔茨海默病和糖尿病的化合物和方法。
• 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.
• 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.