(2S,3S,4R)-1-(α-D-galactopyranosyloxy)-2-[(R)-2-hydroxytetracosanoylamino]-3,4-octadecanediol | 148347-42-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (2S,3S,4R)-1-(α-D-galactopyranosyloxy)-2-[(R)-2-hydroxytetracosanoylamino]-3,4-octadecanediol
• 英文别名: (2R)-N-[(1S,2S,3R)-1-[(I+/--D-Galactopyranosyloxy)methyl]-2,3-dihydroxyheptadecyl]-2-hydroxytetracosanamide；(2R)-N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]-2-hydroxytetracosanamide
• CAS: 148347-42-6
• 化学式: C₄₈H₉₅NO₁₀
• 分子量: 846.283
• InChiKey: ODTUNRBWGNXHMQ-LXKABXHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.2
• 重原子数：
  59
• 可旋转键数：
  42
• 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

• 作为产物：
  描述：

  [(2S,3S,4R)-2-[[(2R)-2-acetyloxytetracosanoyl]amino]-3-benzoyloxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-4-yl] benzoate 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以82%的产率得到(2S,3S,4R)-1-(α-D-galactopyranosyloxy)-2-[(R)-2-hydroxytetracosanoylamino]-3,4-octadecanediol
  参考文献：
  名称：

  Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice

  摘要：

  Agelasphin-9b, (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-16-methyl-2-[N-((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S;4R)-1-O-(alpha-D-galactopyranosyl)2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.

  DOI：

  10.1021/jm00012a018

文献信息

• NOVEL MEDICINAL COMPOSITION
  申请人：KIRIN BEER KABUSHIKI KAISHA

  公开号：EP0650732A1

  公开（公告）日：1995-05-03

  A medicinal composition comprising at least one compound represented by general formula (A), specifically a myeloid cell growth promoter, a radiation damage protective and a thrombocytopenia remedy, wherein R represents (α), (R₂ being H or OH, and X being an integer of 0 to 26) or -(CH₂)₇CH=CH(CH₂)₇CH₃; R₁ represents a substituent selected from the group consisting of -CH₂(CH₂)YCH₃, -CH(OH)(CH₂)YCH₃, -CH(OH)(CH₂)YCH(CH₃)₂ and -CH=CH(CH₂)YCH₃; and Y represents an integer of 5 to 17.

  一种药物组合物，包含至少一种由通式(A)代表的化合物，特别是一种髓系细胞生长促进剂、一种辐射损伤保护剂和一种血小板减少治疗剂，其中 R 代表(α)，(R₂为 H 或 OH，X 为 0 至 26 的整数)或-(CH₂)₇CH=CH(CH₂)₇CH₃；R₁ 代表选自以下组成的组的取代基：-CH₂(CH₂)YCH₃、-CH(OH)(CH₂)YCH₃、-CH(OH)(CH₂)YCH(CH₃)₂ 和 -CH=CH(CH₂)YCH₃；以及 Y 代表 5 至 17 的整数。
• METHOD FOR ACTIVATING HUMAN ANTIGEN PRESENTING CELLS, ACTIVATED HUMAN ANTIGEN PRESENTING CELLS, AND USE OF THE SAME
  申请人：Kirin Brewery Company, Ltd.

  公开号：EP0957161B1

  公开（公告）日：2006-05-10
• 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
• ACTIVATION OF INKT CELLS
  申请人：INSERM - Institut National de la Santé et de la Recherche Médicale

  公开号：EP2958595A1

  公开（公告）日：2015-12-30