2-O-(1,2-O-distearoyl-sn-glycero-3-phoshoryl)-1,3-bis-O-(α-D-mannopyranosyl)glycerol triethylammonium salt | 852395-60-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-(1,2-O-distearoyl-sn-glycero-3-phoshoryl)-1,3-bis-O-(α-D-mannopyranosyl)glycerol triethylammonium salt
• 英文别名: [(2R)-3-[1,3-bis[[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]propan-2-yloxy-hydroxyphosphoryl]oxy-2-octadecanoyloxypropyl] octadecanoate;N,N-diethylethanamine
• CAS: 852395-60-9
• 化学式: C₆H₁₅N*C₅₄H₁₀₃O₂₀P
• 分子量: 1204.57
• InChiKey: AFNAULTVUJIHIF-ZSEORDDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.45
• 重原子数：
  82
• 可旋转键数：
  53
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  314
• 氢给体数：
  9
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  2-O-(1,2-di-O-stearoyl-sn-glycero-3-phosphoryl)-1,3-bis-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)glycerol triethylammonium salt 在 10% palladium on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 18.0h， 以69%的产率得到2-O-(1,2-O-distearoyl-sn-glycero-3-phoshoryl)-1,3-bis-O-(α-D-mannopyranosyl)glycerol triethylammonium salt
  参考文献：
  名称：

  A PIM2 analogue suppresses allergic airway disease

  摘要：

  Two approaches for the synthesis of a phosphatidylinositol dimannoside (PIM2) analogue 4 that mimics the suppressive activity of natural PIMs and also synthetic PIM2 have been developed. This analogue, where the inositol core was replaced by glycerol, was tested for its ability to suppress cellular inflammation in a mouse model of allergic asthma and shown to be effective in suppressing airway eosinophilia. Suppression of all inflammatory cells monitored was observed, indicating a general blockade of cellular activity. These data indicate that the inositol core is not essential for this suppressive activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.058

文献信息

• A PIM2 analogue suppresses allergic airway disease
  作者：Jacquie L. Harper、Colin M. Hayman、David S. Larsen、Gavin F. Painter、Gurmit Singh-Gill

  DOI：10.1016/j.bmc.2010.11.058

  日期：2011.1

  Two approaches for the synthesis of a phosphatidylinositol dimannoside (PIM2) analogue 4 that mimics the suppressive activity of natural PIMs and also synthetic PIM2 have been developed. This analogue, where the inositol core was replaced by glycerol, was tested for its ability to suppress cellular inflammation in a mouse model of allergic asthma and shown to be effective in suppressing airway eosinophilia. Suppression of all inflammatory cells monitored was observed, indicating a general blockade of cellular activity. These data indicate that the inositol core is not essential for this suppressive activity. (C) 2010 Elsevier Ltd. All rights reserved.