3-hydroxy-6-(hydroxymethyl)-2-((5-methoxy-1H-indol-3-yl)(phenyl)methyl)-4H-pyran-4-one

• 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: 3-hydroxy-6-(hydroxymethyl)-2-((5-methoxy-1H-indol-3-yl)(phenyl)methyl)-4H-pyran-4-one
• 英文别名: 3-hydroxy-6-(hydroxymethyl)-2-[(5-methoxy-1H-indol-3-yl)-phenylmethyl]pyran-4-one
• 化学式: C₂₂H₁₉NO₅
• 分子量: 377.397
• InChiKey: NMBYRWGKAYQPGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  91.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲醛 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 3-hydroxy-6-(hydroxymethyl)-2-((5-methoxy-1H-indol-3-yl)(phenyl)methyl)-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 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.