二十四烷酰胺,N-[(1S,2S,3R)-1-[(a-D-半乳吡喃糖氧基)甲基]-2,3-二羟基十五烷基]-2-羟基-,(2R)- | 148347-44-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 二十四烷酰胺,N-[(1S,2S,3R)-1-[(a-D-半乳吡喃糖氧基)甲基]-2,3-二羟基十五烷基]-2-羟基-,(2R)-
• 英文名称: Agelasphin-7a
• 英文别名: (2R)-N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexadecan-2-yl]-2-hydroxytetracosanamide
• CAS: 148347-44-8
• 化学式: C₄₆H₉₁NO₁₀
• 分子量: 818.229
• InChiKey: SCUZCUUKWLRMKB-NQEFSKNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  57
• 可旋转键数：
  40
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  189
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  二十四烷酰胺,N-[(1S,2S,3R)-1-[(a-D-半乳吡喃糖氧基)甲基]-2,3-二羟基十五烷基]-2-羟基-,(2R)- 在 吡啶 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 19.5h， 生成 (2S,3S,4R)-2-acetamino-1,3,4-triacetoxyhexadecane
  参考文献：
  名称：

  Agelasphins, novel antitumor and immunostimulatory cerebrosides from the marine sponge Agelas mauritianus

  摘要：

  New glycosphingolipids, named agelasphins (1-8), have been isolated by antitumor and immunostimulatory bioassay-guided purification from an extract of a marine sponge, Agelas mauritianus. Strongly active agents in agelasphins had characteristic ol-galactosylceramide structures, the isolation of which from natural products has not previously been reported. The absolute configurations of agelasphins were elucidated by the total synthesis.

  DOI：

  10.1016/s0040-4020(01)86991-x
• 作为产物：
  描述：

  (R)-2-Benzyloxy-tetracosanoic acid [(1S,2S,3R)-2,3-bis-benzyloxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-pentadecyl]-amide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 24.0h， 以95%的产率得到二十四烷酰胺,N-[(1S,2S,3R)-1-[(a-D-半乳吡喃糖氧基)甲基]-2,3-二羟基十五烷基]-2-羟基-,(2R)-
  参考文献：
  名称：

  2-Deoxy-disaccharide approach to natural and unnatural glycosphingolipids synthesis

  摘要：

  2-Deoxy-disaccharides were easily converted into glycosylphytosphingosines, as new and efficient precursors of natural and unnatural glycosphingolipids. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00366-9

文献信息

• Alpha gylcosylceramides for treating bacterial and fungal infections
  申请人：——

  公开号：US20020115624A1

  公开（公告）日：2002-08-22

  This invention relates to methods and compositions for the treatment of bacterial or fungal infectious disease, and to methods and compositions for screening assays to select agents that are useful for this purpose. In particular the invention relates to alpha-glycosylceramide molecules and their use in treating such infectious disease.

  本发明涉及用于治疗细菌或真菌感染病的方法和组合物，以及用于筛选筛选试剂的方法和组合物，以选择对此目的有用的试剂。特别地，本发明涉及α-糖基鞘脂分子及其在治疗此类感染病方面的应用。
• NOVEL SPHINGOGLYCOLIPID AND USE THEREOF
  申请人：KIRIN BEER KABUSHIKI KAISHA

  公开号：EP0609437B1

  公开（公告）日：1999-07-07
• METHODS AND PHARMACEUTICAL COMPOSITIONS FOR THE PROPHYLACTIC TREATMENT OF BACTERIAL SUPERINFECTIONS POST-INFLUENZA WITH INVARIANT NKT CELL AGONISTS
  申请人：INSERM - Institut National de la Santé et de la Recherche Médicale

  公开号：EP2903622A1

  公开（公告）日：2015-08-12
• METHODS AND PHARMACEUTICAL COMPOSITIONS FOR THE TREATMENT OF ACUTE EXACERBATIONS OF CHRONIC OBSTRUCTIVE PULMONARY DISEASE
  申请人：INSERM (Institut National de la Santé et de la Recherche Médicale)

  公开号：EP3104864A1

  公开（公告）日：2016-12-21
• ACTIVATION OF iNKT CELLS
  申请人：INSERM (INSTITUT NATIONAL DE LA SANTÉ ET DE LA RECHERCHE MÉDICALE

  公开号：US20150374734A1

  公开（公告）日：2015-12-31

  The present invention relates to particulate entity, such as a nanoparticle or conjugate, for use in particular as adjuvant in vaccine or immunotherapy. More specifically, the invention relates to a particulate entity comprising: iv. an iNKT cell agonist such as α Gal Car compound, and, v. one or more antigenic determinant(s) such as a tumour antigen(s) or pathogen-derived antigen(s), vi. a targeting agent that targets in vivo said iNKT cell agonist to dendritic cells, such as human BDCA3+ dendritic cells.