(2R*)-2-(O-benzoyl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)glycerol | 852395-53-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (2R*)-2-(O-benzoyl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)glycerol
• 英文别名: 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)glycerol；2-O-Benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-alpha-D-mannopyranosyl)glycerol；[1-hydroxy-3-[(2S,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropan-2-yl] benzoate
• CAS: 852395-53-0
• 化学式: C₄₄H₄₆O₉
• 分子量: 718.844
• InChiKey: ZZCZEYUVWBRACO-MMENLPHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  53
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R*)-2-(O-benzoyl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)glycerol 、 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl dimethyl phosphite 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 乙醚 为溶剂， 反应 2.25h， 生成 (2R*)-2-O-benzoyl-1,3-bis-O-(2,3,4,6-tetra-O-benzyl-D-mannopyranosyl)glycerol 、 (2R*)-2-O-benzoyl-1,3-bis-O-(2,3,4,6-tetra-O-benzyl-D-mannopyranosyl)glycerol
  参考文献：
  名称：

  [EN] SYNTHETIC MOLECULES HAVING IMMUNE ACTIVITY
  [FR] MOLECULES SYNTHETIQUES A IMMUNO-ACTIVITE

  摘要：

  本发明涉及具有类似于PIM（酰基甘油磷脂肌醇寡糖）活性的合成分子，用于治疗和预防炎症性或免疫细胞介导的疾病或紊乱。

  公开号：

  WO2005049631A1
• 作为产物：
  描述：

  (3S,4S,5R,6R)-2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran 在 吡啶 、 四氧化锇 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 1.5h， 生成 (2R*)-2-(O-benzoyl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)glycerol
  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

• [EN] SYNTHETIC MOLECULES HAVING IMMUNE ACTIVITY<br/>[FR] MOLECULES SYNTHETIQUES A IMMUNO-ACTIVITE
  申请人：MALAGHAN INST OF MEDICAL RES

  公开号：WO2005049631A1

  公开（公告）日：2005-06-02

  The present invention is directed to synthetic molecules having biological activity similar to PIM (acyl glycerol phosphatidylinositol manno-oligosaccharide) activity, for use in the treatment and prevention of inflammatory or immune cell mediated diseases or disorders.

  本发明涉及具有类似于PIM（酰基甘油磷脂肌醇寡糖）活性的合成分子，用于治疗和预防炎症性或免疫细胞介导的疾病或紊乱。
• Synthetic Molecules Having Immune Activity
  申请人：Singh-Gill Gurmit

  公开号：US20080249037A1

  公开（公告）日：2008-10-09

  The present invention is directed to synthetic molecules having biological activity similar to PIM (acyl glycerol phosphatidylinositol manno-oligosacccharide) activity, for use in the treatment and prevention of inflammatory or immune cell mediated diseases or disorders.

  本发明涉及具有类似于PIM（酰基甘油磷酰肌醇低聚糖）活性的合成分子，用于治疗和预防由炎症或免疫细胞介导的疾病或障碍。
• Synthetic molecules having immune activity
  申请人：The Malaghan Institute of Medical Research

  公开号：US07989602B2

  公开（公告）日：2011-08-02

  The present invention is directed to synthetic molecules having biological activity similar to PIM (acyl glycerol phosphatidylinositol manno-oligosaccharide) activity, for use in the treatment and prevention of inflammatory or immune cell mediated diseases or disorders.

  本发明涉及具有类似于PIM（酰基甘油磷酰肌醇甘露寡糖）活性的合成分子，用于治疗和预防炎症或免疫细胞介导的疾病或障碍。
• US7989602B2
  申请人：——

  公开号：US7989602B2

  公开（公告）日：2011-08-02
• 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.