1-O-allyl-3-O-benzyl-2-O-hexadecyl-sn-glycerol | 945491-72-5

• 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: 1-O-allyl-3-O-benzyl-2-O-hexadecyl-sn-glycerol
• 英文别名: [(2R)-2-hexadecoxy-3-prop-2-enoxypropoxy]methylbenzene
• CAS: 945491-72-5
• 化学式: C₂₉H₅₀O₃
• 分子量: 446.714
• InChiKey: DTOXBJNJPXEWHT-GDLZYMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  32
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-O-allyl-3-O-benzyl-2-O-hexadecyl-sn-glycerol 在 四(三苯基膦)钯 吡啶 、 1,3-二甲基巴比妥酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 52.0h， 生成 3-O-benzyl-1-O-hexadecanoyl-2-O-hexadecyl-sn-glycerol
  参考文献：
  名称：

  Phosphatidylinositol Mannoside Ether Analogues:  Syntheses and Interleukin-12-Inducing Properties

  摘要：

  Phosphatidylinositol mannosides (PIMs) isolated from mycobacteria have been identified as an important class of glycolipids with significant immune modulating properties. We present here the syntheses of phosphatidylinositol dimannoside ether analogues 2 and 3 and evaluate their interleukin-12 (IL-12)-inducing properties along with dipalmitoyl PIM2 (1) in an in vitro bovine dendritic cell assay. Both synthetic PIM analogues and synthetic dipalmitoyl PIM2 (1) were effective at enhancing IL-12 production by immature bovine dendritic cells. Unexpectedly, ether analogue 2 was significantly more active than dipalmitoyl PIM2 (1) which indicates that modified PIM compounds can be strongly immunoactive and may have significant adjuvant activities.

  DOI：

  10.1021/jo070639m
• 作为产物：
  描述：

  (R)-苄氧甲基环氧乙烷 在 三氟化硼乙醚 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 1-O-allyl-3-O-benzyl-2-O-hexadecyl-sn-glycerol
  参考文献：
  名称：

  Phosphatidylinositol Mannoside Ether Analogues:  Syntheses and Interleukin-12-Inducing Properties

  摘要：

  Phosphatidylinositol mannosides (PIMs) isolated from mycobacteria have been identified as an important class of glycolipids with significant immune modulating properties. We present here the syntheses of phosphatidylinositol dimannoside ether analogues 2 and 3 and evaluate their interleukin-12 (IL-12)-inducing properties along with dipalmitoyl PIM2 (1) in an in vitro bovine dendritic cell assay. Both synthetic PIM analogues and synthetic dipalmitoyl PIM2 (1) were effective at enhancing IL-12 production by immature bovine dendritic cells. Unexpectedly, ether analogue 2 was significantly more active than dipalmitoyl PIM2 (1) which indicates that modified PIM compounds can be strongly immunoactive and may have significant adjuvant activities.

  DOI：

  10.1021/jo070639m

文献信息

• ANALOGUES OF PHOSPHATIDYLINOSITOL MANNOSIDES
  申请人：Ainge Gary David

  公开号：US20100297156A1

  公开（公告）日：2010-11-25

  The invention relates to compounds which are immunomodulatory compounds and, in particular, can induce IL-12 secretion. The invention also relates to compositions containing the compounds, precursors, and prodrugs of these compounds, use of these compounds as adjuvants in combination with vaccines, and use of these compounds for treatment of diseases or conditions relating to infection, atopic disorders, or cancer.

  本发明涉及免疫调节化合物，特别是能够诱导IL-12分泌的化合物。本发明还涉及包含这些化合物、前体和前药的组合物，这些化合物作为疫苗佐剂的使用，以及这些化合物用于治疗与感染、特应性疾病或癌症相关的疾病或病症的使用。
• WO2008/75983
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] ANALOGUES OF PHOSPHATIDYLINOSITOL MANNOSIDES<br/>[FR] ANALOGUES DES PHOSPHATIDYLINOSITOL MANNOSIDES
  申请人：IND RES LTD

  公开号：WO2008075983A2

  公开（公告）日：2008-06-26

  [EN] The invention relates to compounds which are immunomodulatory compounds and, in particular, can induce IL-12 secretion. The invention also relates to compositions containing the compounds, precursors, and prodrugs of these compounds, use of these compounds as adjuvants in combination with vaccines, and use of these compounds for treatment of diseases or conditions relating to infection, atopic disorders, or cancer.
  [FR] L'invention concerne des composés qui sont des composés immunomodulateurs et, en particulier, qui peuvent induire la sécrétion de l'IL-12. L'invention concerne également des compositions contenant lesdits composés, des précurseurs et des promédicaments de ces composés, l'utilisation de ces composés en tant qu'adjuvants en association avec des vaccins et l'utilisation de ces composés pour le traitement de maladies ou affections concernant une infection, des troubles atopiques ou un cancer.