4-(β-D-glucopyrfmanosyloxy)phenyl benzoate | 4106-97-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 4-(β-D-glucopyrfmanosyloxy)phenyl benzoate
• 英文别名: 4-(β-D-glucopyranosyloxy)phenyl benzoate
• CAS: 4106-97-2
• 化学式: C₁₉H₂₀O₈
• 分子量: 376.363
• InChiKey: QQHOBCWHPYYAMV-OGJJZOIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.08
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  125.68
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenylbenzoate 在 盐酸 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 生成 4-(β-D-glucopyrfmanosyloxy)phenyl benzoate
  参考文献：
  名称：

  水杨素，沙雷平和熊果苷的酰基衍生物的合成

  摘要：

  水杨科的两种天然酚糖苷的总合成物：populoside和2-（β-d-吡喃吡喃糖基氧基）-5-羟基苄基（3-甲氧基-4-羟基）肉桂酸酯和九种在植物中尚未发现的酰基衍生物酚苷：2-（β-d-吡喃葡萄糖基氧基）-苄基肉桂酸酯，2-（β-d-吡喃葡萄糖基氧基）-苄基（4-羟基）苯甲酸酯，2-（β-d-吡喃葡萄糖基氧基）-苄基（3-甲氧基-4-羟基）苯甲酸酯，2-（β-d-吡喃葡萄糖基氧基）-5-羟基苄基（3,4-二羟基）肉桂酸酯，2-（β-d-吡喃葡萄糖基氧基）-5-羟基苄基肉桂酸酯，2-（β-d-吡喃葡萄糖基氧基）-5-羟基苄基（4-羟基）苯甲酸酯，2-（β-d-吡喃葡萄糖基氧基）-5-羟基苄基（3-甲氧基-4-羟基）苯甲酸酯，2-（β-d-吡喃葡萄糖基氧基）-5-苯甲酰氧基苄基苯甲酸酯和4-（β-d-吡喃葡萄糖基氧基）-苯甲酸酯从容易获得的苯酚开始，葡萄糖首次被开发出来。

  DOI：

  10.1016/j.carres.2014.02.014

文献信息

• Glucosylpolyphenols as Inhibitors of Aβ-Induced Fyn Kinase Activation and Tau Phosphorylation: Synthesis, Membrane Permeability, and Exploratory Target Assessment within the Scope of Type 2 Diabetes and Alzheimer’s Disease
  作者：Ana M. de Matos、M. Teresa Blázquez-Sánchez、Andreia Bento-Oliveira、Rodrigo F. M. de Almeida、Rafael Nunes、Pedro E. M. Lopes、Miguel Machuqueiro、Joana S. Cristóvão、Cláudio M. Gomes、Cleide S. Souza、Imane G. El Idrissi、Nicola A. Colabufo、Ana Diniz、Filipa Marcelo、M. Conceição Oliveira、Óscar López、José G. Fernandez-Bolaños、Philipp Dätwyler、Beat Ernst、Ke Ning、Claire Garwood、Beining Chen、Amélia P. Rauter

  DOI：10.1021/acs.jmedchem.0c00841

  日期：2020.10.22

  Despite the rapidly increasing number of patients suffering from type 2 diabetes, Alzheimer's disease, and diabetes-induced dementia, there are no disease-modifying therapies that are able to prevent or block disease progress. In this work, we investigate the potential of nature-inspired glucosylpolyphenols against relevant targets, including islet amyloid polypeptide, glucosidases, and cholinesterases. Moreover, with the premise of Fyn kinase as a paradigm-shifting target in Alzheimer's drug discovery, we explore glucosylpolyphenols as blockers of Aβ-induced Fyn kinase activation while looking into downstream effects leading to Tau hyperphosphorylation. Several compounds inhibit Aβ-induced Fyn kinase activation and decrease pTau levels at 10 μM concentration, particularly the per-O-methylated glucosylacetophloroglucinol and the 4-glucosylcatechol dibenzoate, the latter inhibiting also butyrylcholinesterase and β-glucosidase. Both compounds are nontoxic with ideal pharmacokinetic properties for further development. This work ultimately highlights the multitarget nature, fine structural tuning capacity, and valuable therapeutic significance of glucosylpolyphenols in the context of these metabolic and neurodegenerative disorders.