(2S,3R,4R)-3,4-dihydroxy-2-(hexacosanoyloxy)octadecyl α-D-galactopyranoside | 1215176-69-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3R,4R)-3,4-dihydroxy-2-(hexacosanoyloxy)octadecyl α-D-galactopyranoside
• 英文别名: (2S,3R,4R)-2-hexacosanoyloxy-3,4-dihydroxyoctadecyl α-D-galactopyranoside；(2S,3R,4R)-3,4-dihydroxy-2-hexacosanoyloxyoctadecyl α-D-galactopyranoside；[(2S,3R,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl] hexacosanoate
• CAS: 1215176-69-4
• 化学式: C₅₀H₉₈O₁₀
• 分子量: 859.322
• InChiKey: ARCHXOATLJQJHG-HAJKCKTJSA-N

物化性质

• 沸点：
  896.2±65.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.6
• 重原子数：
  60
• 可旋转键数：
  45
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4,6-O-isopropylidene-2,3-di-O-4-methoxybenzyl-α-D-galactopyranose 在 20% palladium hydroxide-activated charcoal 4-二甲氨基吡啶 、 氢氟酸 、 水 、 氢气 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氯乙腈 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 122.75h， 生成 (2S,3R,4R)-3,4-dihydroxy-2-(hexacosanoyloxy)octadecyl α-D-galactopyranoside
  参考文献：
  名称：

  ESTERIFIED ALPHA-GALACTOSYLCERAMIDE

  摘要：

  该发明提供了用于癌症治疗等的酯化α-半乳糖鞘氨醇，以及含有该酯化物的药物。具体来说，该发明涉及一种由以下式表示的化合物（I）： 其中R1是具有1至30个碳原子数的烃基，R2是具有1至20个碳原子数的烃基，R3是氢原子或具有1至5个碳原子数的烃基，R4和R5相同或不同，每个都是氢原子或具有1至5个碳原子数的烃基，或者R4和R5结合在一起形成具有1至5个碳原子数的二价烃基，且可选择地与邻近的乙二醚氧形成环结构，或其盐。

  公开号：

  US20110224158A1

文献信息

• Synthesis and biological activity of ester and ether analogues of α-galactosylceramide (KRN7000)
  作者：Masao Shiozaki、Takuya Tashiro、Hiroyuki Koshino、Ryusuke Nakagawa、Sayo Inoue、Tomokuni Shigeura、Hiroshi Watarai、Masaru Taniguchi、Kenji Mori

  DOI：10.1016/j.carres.2010.05.003

  日期：2010.8

  (alphaGalCer, KRN7000) has been identified as a modulator of immunological processes through its capacity to bind iNKT cells mediated by CD1d molecules. Some analogues in while the amide group in alphaGalCer is replaced with ester or ether groups were synthesized from d-arabinitol or l-ribose to evaluate their ability to activate iNKT cells. Ester analogues 30a, 31a, and 61 showed activity for IFNgamma

  α-半乳糖苷神经酰胺（alphaGalCer，KRN7000）由于具有结合CD1d分子介导的iNKT细胞的能力，已被鉴定为免疫过程的调节剂。从d-阿拉伯糖醇或l-核糖合成了alphaGalCer中的酰胺基被酯或醚基取代时的一些类似物，以评估其激活iNKT细胞的能力。酯类似物30a，31a和61显示出对iNKT细胞产生IFNγ和IL-4的活性，而α-半乳糖基神经酰胺的醚（31b）和4-甲氧基酯（76）类似物对iNKT细胞没有活性。
• ESTERIFIED ALPHA-GALACTOSYLCERAMIDE
  申请人：Shiozaki Masao

  公开号：US20110224158A1

  公开（公告）日：2011-09-15

  The invention provides esterified α-galactosylceramides effective for cancer treatment and the like, and a medicament containing same. In particular, the invention relates to a compound represented by the formula (I): wherein R 1 is a hydrocarbon group having a carbon number of 1 to 30, R 2 is a hydrocarbon group having a carbon number of 1 to 20, R 3 is a hydrogen atom or hydrocarbon group having a carbon number of 1 to 5, R 4 and R 5 are the same or different and each is a hydrogen atom or a hydrocarbon group having a carbon number of 1 to 5, or R 4 and R 5 in combination form a divalent hydrocarbon group having a carbon number of 1 to 5, and optionally form a ring structure together with the adjacent ethylenedioxy, or a salt thereof.

  该发明提供了用于癌症治疗等的酯化α-半乳糖鞘氨醇，以及含有该酯化物的药物。具体来说，该发明涉及一种由以下式表示的化合物（I）： 其中R1是具有1至30个碳原子数的烃基，R2是具有1至20个碳原子数的烃基，R3是氢原子或具有1至5个碳原子数的烃基，R4和R5相同或不同，每个都是氢原子或具有1至5个碳原子数的烃基，或者R4和R5结合在一起形成具有1至5个碳原子数的二价烃基，且可选择地与邻近的乙二醚氧形成环结构，或其盐。
• Synthesis and biological activity of hydroxylated analogs of RCAI-80
  作者：Masao Shiozaki、Takuya Tashiro、Hiroyuki Koshino、Tomokuni Shigeura、Hiroshi Watarai、Masaru Taniguchi、Kenji Mori

  DOI：10.1016/j.tet.2013.09.029

  日期：2013.11

  RCAI-80 is one of the ester analogs of KRN7000 (alpha-galactosylceramide). This compound released mainly T helper 2 (Th2) cytokines, such as IL-4 rather than T helper 1 (Th1) cytokines, such as IFN gamma from the invariant natural killer T (iNKT) cells. In addition, it has been known that some of the hydroxylated derivatives of KRN7000 make the cytokine secretion bias to Th2 by decreasing the IFN gamma production to almost zero. This time, the three compounds having these two characteristic properties, namely an ester group and also some extra hydroxy groups existing on the ester side chain and/or on the 2-acyloxy-3,4dihydroxyoctadecyl main chain of RCAI-80, were synthesized to examine the biological activities. As a result, it was found that these compounds made the cytokine secretion skew to Th2. Therefore, their effectiveness for experimental autoimmune encephalomyelitis (EAE) was examined. It was recognized that one of them showed moderate suppression of EAE symptom. (c) 2013 Elsevier Ltd. All rights reserved.
• US8580751B2
  申请人：——

  公开号：US8580751B2

  公开（公告）日：2013-11-12
• ESTERIFIED ALPHA-GALACTOSYLCERAMIDE
  申请人：Riken

  公开号：EP2336144B1

  公开（公告）日：2015-01-21