1-(2,3,4,6-tetra-O-methyl-β-D-glucopyranosyl)naphthalen-2-ol | 120649-51-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,3,4,6-tetra-O-methyl-β-D-glucopyranosyl)naphthalen-2-ol
• 英文别名: 1-[(2S,3S,4R,5R,6R)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]naphthalen-2-ol
• CAS: 120649-51-6
• 化学式: C₂₀H₂₆O₆
• 分子量: 362.423
• InChiKey: RVHFHJOTBMBLJC-LGKHCZOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-fluorophenyl 2,3,4,6-tetra-O-methyl-1-thio-β-D-glucopyranoside 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 1-(2,3,4,6-tetra-O-methyl-β-D-glucopyranosyl)naphthalen-2-ol
  参考文献：
  名称：

  碳正离子的闪速电化学方法

  摘要：

  开发了一种新型流动电化学反应器，可在几秒钟内完成电解，能够快速生成短寿命碳阳离子，并在亲核试剂分解之前捕获反应。本方法适用于高反应性氧代碳鎓离子、N-酰基亚胺离子、糖基阳离子和费里尔阳离子。此外，成功地证明了使用流动反应器系统连续和快速合成药物前体。

  DOI：

  10.1002/anie.202116177

文献信息

• Boron Trifluoride-Catalyzed Rearrangement of 2-Aryloxytetrahydropyrans: A New Entry to C-Arylglycosidation
  作者：Tadashi Kometani、Hiroyuki Kondo、Yukio Fujimori

  DOI：10.1055/s-1988-27788

  日期：——

  Treatment of 2-aryloxytetrahydropyrans with boron trifluoride afforded 2-aryltetrahydropyrans via rearrangement in good yield. Aryl O-glycopyranosides were converted into the corresponding C-glycopyranosides by the same procedure.

  使用三氟化硼处理2-芳氧基四氢吡喃，可以通过重排反应高效地得到2-芳基四氢吡喃。同样的方法可以将芳基O-糖苷转化为相应的C-糖苷。
• 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.