methyl 4,6-O-(4-methoxybenzylidene)-2,3-di-O-tetradecyl-α-D-glucopyranoside | 872677-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 4,6-O-(4-methoxybenzylidene)-2,3-di-O-tetradecyl-α-D-glucopyranoside
• CAS: 872677-64-0
• 化学式: C₄₃H₇₆O₇
• 分子量: 705.072
• InChiKey: UPHHCUZDEONZAE-NABDUZDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.65
• 重原子数：
  50.0
• 可旋转键数：
  31.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-(4-methoxybenzylidene)-2,3-di-O-tetradecyl-α-D-glucopyranoside 在 吡啶 、 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 methyl 4-O-(4-methoxybenzyl)-2,3-di-O-tetradecyl-α-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime
  参考文献：
  名称：

  WO2007/107285

  摘要：

  公开号：
• 作为产物：
  描述：

  溴代十四烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以74%的产率得到methyl 4,6-O-(4-methoxybenzylidene)-2,3-di-O-tetradecyl-α-D-glucopyranoside
  参考文献：
  名称：

  WO2007/107285

  摘要：

  公开号：

文献信息

• Trehalose- and Glucose-Derived Glycoamphiphiles: Small-Molecule and Nanoparticle Toll-Like Receptor 4 (TLR4) Modulators
  作者：Julio Rodriguez Lavado、Stefania E. Sestito、Roberto Cighetti、Eva M. Aguilar Moncayo、Alja Oblak、Duško Lainšček、José Luis Jiménez Blanco、José Manuel García Fernández、Carmen Ortiz Mellet、Roman Jerala、Valentina Calabrese、Francesco Peri

  DOI：10.1021/jm501182w

  日期：2014.11.13

  An increasing number of pathologies have been linked to Toll-like receptor 4 (TLR4) activation and signaling, therefore new hit and lead compounds targeting this receptor activation process are urgently needed. We report on the synthesis and biological properties of glycolipids based on glucose and trehalose scaffolds which potently inhibit TLR4 activation and signaling in vitro and in vivo. Structure-activity relationship studies on these compounds indicate that the presence of fatty ester chains in the molecule is a primary prerequisite for biological activity and point to facial amphiphilicity as a preferred architecture for TLR4 antagonism. The cationic glycolipids here presented can be considered as new lead compounds for the development of drugs targeting TLR4 activation and signaling in infectious, inflammatory, and autoimmune diseases. Interestingly, the biological activity of the best drug candidate was retained after adsorption at the surface of colloidal gold nanoparticles, broadening the options for clinical development.