2-((1H-indol-3-yl)(naphthalene-3-yl)methyl)-3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one | 1620408-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((1H-indol-3-yl)(naphthalene-3-yl)methyl)-3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one
• 英文别名: 2-((1H-indol-3-yl)(naphthalen-2-yl)methyl)-3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one；3-hydroxy-6-(hydroxymethyl)-2-[1H-indol-3-yl(naphthalen-2-yl)methyl]pyran-4-one
• CAS: 1620408-29-8
• 化学式: C₂₅H₁₉NO₄
• 分子量: 397.43
• InChiKey: FPADFFFDWBYWKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  82.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  曲酸 、 2-萘甲醛 在 三乙烯二胺 、 silica gel supported sulfuric acid 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 26.0h， 生成 2-((1H-indol-3-yl)(naphthalene-3-yl)methyl)-3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis of heteroaryl/aryl kojic acid conjugates as stimulators of glucose uptake by GLUT4 translocation

  摘要：

  Insulin exerts its metabolic actions through the insulin receptor (IR) and plays an essential role in treatment of diabetes. The inconvenience of daily injections and the undesirable side-effects associated with insulin injections demand novel drugs for the disease. To search for bioactive insulin mimetic, we synthesized a chemical library of small molecules (2a-3f) based on the indolylkojic acid scaffold (B). An In vitro screening assay was performed to stimulate glucose transport in rat L6 skeletal muscle cells, post treatment of the compounds (2a-3f) for the time period incubation of 16 h. Compounds 2f, 2g, 21, 3a, 3b, 3c and 3d have shown significant glucose uptake stimulation as compared to the controls at micromolar concentrations. In mechanistic studies, we observed that these compounds exert their biological action by enhancing GLUT4 translocation to cell surface via PI3K-dependent signalling pathway in agreement to the insulin mode of action. Hence, these promising conjugates should be useful for further drug development in diabetes treatment. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.041

文献信息

• Synthesis of FAU Zeolite Nanoparticles as Heterogeneous Catalyst for One-Pot Synthesis of 2-Substituted Aryl (Indolyl) Kojic Acid Derivatives under Solvent-Free Condition
  作者：Bahareh Sadeghi、Zahra Lasemi、Fereshteh Amiri Tavasoli、Saeedeh Hashemian、Hesam Zahedi

  DOI：10.1080/15533174.2013.818019

  日期：2014.11.26

  have been found to be a highly efficient and versatile catalyst for preparation of 2-substituted aryl (indolyl) kojic acid derivatives through one-pot condensation of kojic acid with aryl aldehydes and indoles under solvent-free conditions. The corresponding products were obtained in very high yields and in short reaction times.

  已经发现，FAU沸石纳米颗粒是用于在无溶剂条件下通过曲酸与芳基醛和吲哚的一锅缩合制备2-取代的芳基（吲哚基）曲酸衍生物的高效且通用的催化剂。以非常高的产率和较短的反应时间获得了相应的产物。
• Synthesis of heteroaryl/aryl kojic acid conjugates as stimulators of glucose uptake by GLUT4 translocation
  作者：Deepak K. Sharma、Jyotsana Pandey、Akhilesh K. Tamrakar、Debaraj Mukherjee

  DOI：10.1016/j.ejmech.2014.08.041

  日期：2014.10

  Insulin exerts its metabolic actions through the insulin receptor (IR) and plays an essential role in treatment of diabetes. The inconvenience of daily injections and the undesirable side-effects associated with insulin injections demand novel drugs for the disease. To search for bioactive insulin mimetic, we synthesized a chemical library of small molecules (2a-3f) based on the indolylkojic acid scaffold (B). An In vitro screening assay was performed to stimulate glucose transport in rat L6 skeletal muscle cells, post treatment of the compounds (2a-3f) for the time period incubation of 16 h. Compounds 2f, 2g, 21, 3a, 3b, 3c and 3d have shown significant glucose uptake stimulation as compared to the controls at micromolar concentrations. In mechanistic studies, we observed that these compounds exert their biological action by enhancing GLUT4 translocation to cell surface via PI3K-dependent signalling pathway in agreement to the insulin mode of action. Hence, these promising conjugates should be useful for further drug development in diabetes treatment. (C) 2014 Elsevier Masson SAS. All rights reserved.