2,5-dihydroxy-3-(1-methyl-1H-indol-3-yl)-6-phenyl-2,5-cyclohexadiene-1,4-dione

• 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: 2,5-dihydroxy-3-(1-methyl-1H-indol-3-yl)-6-phenyl-2,5-cyclohexadiene-1,4-dione
• 英文别名: 2,5-dihydroxy-3-(1-methyl-1H-indol-3-yl)-6-phenyl-[1,4]-benzoquinone；Irtk activator；2,5-dihydroxy-3-(1-methylindol-3-yl)-6-phenylcyclohexa-2,5-diene-1,4-dione
• 化学式: C₂₁H₁₅NO₄
• 分子量: 345.354
• InChiKey: ACJHLQAJKHNUGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  79.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-hydroxy-6-(1-methylindol-3-ylmethylene)-4-phenyl-2H-pyran-2,5(6H)-dione 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以96%的产率得到2,5-dihydroxy-3-(1-methyl-1H-indol-3-yl)-6-phenyl-2,5-cyclohexadiene-1,4-dione
  参考文献：
  名称：

  发现一种有效，高度选择性和口服有效的胰岛素受体小分子活化剂。

  摘要：

  合成了一系列3,6-二芳基-2,5-二羟基苯醌，并评估了其选择性激活人胰岛素受体酪氨酸激酶（IRTK）的能力。2、5-二羟基-6-（1-甲基吲哚-3-基）-3-苯基-1,4-苯醌（2h）被确定为有效，高选择性和口服活性的小分子胰岛素受体活化剂。它以300 nM的EC（50）激活IRTK，并且在浓度高达30,000 nM的情况下不诱导紧密相关的受体（IGFIR，EGFR和PDGFR）的激活。向高血糖db / db小鼠（0.1-10 mg / kg /天）口服给予该化合物可引起剂量依赖性完全或几乎完全纠正高血糖。在ob / ob小鼠中，该化合物（10 mg / kg）导致高胰岛素血症明显减少。在IRTK分析中不起作用的结构相关化合物2c，在相同的暴露水平下未能影响db / db小鼠的血糖水平。化合物2h的其他研究结果旨在评估经典的醌相关现象，为进行更广泛的毒理学评估提供了足够的乐观理由。

  DOI：

  10.1021/jm000285q

文献信息

• SMALL MOLECULE INSULIN MIMETICS ABSENT QUINONES
  申请人：Pirrung C. Michael

  公开号：US20070232663A1

  公开（公告）日：2007-10-04

  Compounds of Formula I are described along with pharmaceutical formulations thereof, and methods of treating disorders such as diabetes and neurodegenerative diseases with such compounds.

  公式I的化合物以及其药物配方被描述，以及使用这些化合物治疗糖尿病和神经退行性疾病的方法。
• Methods and compositions for prevention and treatment of diabetic and aged skin
  申请人：HealOr Ltd.

  公开号：EP2452686A2

  公开（公告）日：2012-05-16

  The present invention relates to methods and compositions for prevention and/or treatment of skin pathologies and disorders associated with diabetes and/or aging. More particularly, the present invention relates to the use of various agents capable of restoring impaired physiological conditions of the skin associated with skin pathologies or disorders.

  本发明涉及预防和/或治疗与糖尿病和/或衰老有关的皮肤病变和紊乱的方法和组合物。更具体地说，本发明涉及能够恢复与皮肤病变或紊乱有关的皮肤受损生理状况的各种制剂的使用。
• Methods and compositions for prevention of diabetic and aged skin
  申请人：HealOr Ltd.

  公开号：EP2452691A2

  公开（公告）日：2012-05-16

  The present invention relates to methods and compositions for prevention and/or treatment of skin pathologies and disorders associated with diabetes and/or aging. More particularly, the present invention relates to the use of various agents capable of restoring impaired physiological conditions of the skin associated with skin pathologies or disorders.

  本发明涉及预防和/或治疗与糖尿病和/或衰老有关的皮肤病变和紊乱的方法和组合物。更具体地说，本发明涉及能够恢复与皮肤病变或紊乱有关的皮肤受损生理状况的各种制剂的使用。
• METHODS AND COMPOSITIONS FOR PREVENTION AND TREATMENT OF DIABETIC AND AGED SKIN
  申请人：Healor Ltd.

  公开号：EP1940440A2

  公开（公告）日：2008-07-09
• METHOD AND COMPOSITIONS FOR PREVENTION AND TREATMENT OF DIABETIC AND AGED SKIN
  申请人：Tennenbaum Tamar

  公开号：US20110021422A1

  公开（公告）日：2011-01-27

  Method and compositions are provided for treating or preventing a skin pathology or disorder associated with diabetes and/or aging, by topical administration of at least one agent capable of restoring an impaired physiological condition of the skin associated with said skin pathology or disorder. Examples of such agents include PKC modulating agents, various adipokines and insulin signaling related molecules. In particular, restoration of the subcutaneous adipose tissue can overcome many of the diabetic skin pathologies and aging skin disorders and conditions.