2-(6-benzoyl-β-glucopyranosyloxy)-5-ethoxybenzyl alcohol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(6-benzoyl-β-glucopyranosyloxy)-5-ethoxybenzyl alcohol
• 英文别名: [(2R,3S,4S,5R,6S)-6-[4-ethoxy-2-(hydroxymethyl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl benzoate
• 化学式: C₂₂H₂₆O₉
• 分子量: 434.443
• InChiKey: RVTNQKBVGOQLGP-OUUKCGNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  硫酸二乙酯 、 Nigracin; 4-羟基-2-(羟基甲基)苯基 6-苯甲酰 beta-D-吡喃葡萄糖苷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以25%的产率得到2-(6-benzoyl-β-glucopyranosyloxy)-5-ethoxybenzyl alcohol
  参考文献：
  名称：

  Poliothrysoside and its derivatives as novel insulin sensitizers potentially driving AMPK activation and inhibiting adipogenesis

  摘要：

  In our efforts to develop safe and active chemical entities from nature, we first identified poliothrysoside (1), a phytoconstituent isolated from Flacourtia indica, possessing antidiabetic potential. Subsequently, fifteen derivatives (2-16) were synthesized to assess the activity profile of this class. All the compounds were analyzed for their glucose uptake potency in chronic insulin-induced insulin resistant 3T3-L1 adipocytes. Interestingly, compound 2 exhibited strong ability to increase the insulin sensitivity, primarily activating the AMPK signaling pathway and also inhibited the adipogenesis in 3T3-L1 adipocytes, in concentration dependent manner. Overall, these studies suggest the potential of poliothrysoside and its derivatives as promising leads for non-insulin dependent type 2 diabetes (T2D). (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.015

文献信息

• Poliothrysoside and its derivatives as novel insulin sensitizers potentially driving AMPK activation and inhibiting adipogenesis
  作者：Koneni V. Sashidhara、Suriya P. Singh、Salil Varshney、Muheeb Beg、Anil N. Gaikwad

  DOI：10.1016/j.ejmech.2014.09.015

  日期：2014.10

  In our efforts to develop safe and active chemical entities from nature, we first identified poliothrysoside (1), a phytoconstituent isolated from Flacourtia indica, possessing antidiabetic potential. Subsequently, fifteen derivatives (2-16) were synthesized to assess the activity profile of this class. All the compounds were analyzed for their glucose uptake potency in chronic insulin-induced insulin resistant 3T3-L1 adipocytes. Interestingly, compound 2 exhibited strong ability to increase the insulin sensitivity, primarily activating the AMPK signaling pathway and also inhibited the adipogenesis in 3T3-L1 adipocytes, in concentration dependent manner. Overall, these studies suggest the potential of poliothrysoside and its derivatives as promising leads for non-insulin dependent type 2 diabetes (T2D). (C) 2014 Elsevier Masson SAS. All rights reserved.