RCAI-61 | 1092684-40-6

• 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: RCAI-61
• 英文别名: (2S,3S,4R)-1-O-(6-O-methyl-α-D-galactopyranosyl)-2-(hexacosanamido)octadecane-1,3,4-triol；(2S,3S,4R)-1-O-(6-O-methyl-α-D-galactopyranosyl)-D-ribo-2-hexacosanoylamino-1,3,4-octadecantriol；N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methoxymethyl)oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide
• CAS: 1092684-40-6
• 化学式: C₅₁H₁₀₁NO₉
• 分子量: 872.364
• InChiKey: RLJXSMPFCRRZAF-SVYZMDQNSA-N

物化性质

• 沸点：
  927.8±65.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16
• 重原子数：
  61
• 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：
  158
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2S,3S,4R)-3,4-二[(叔-丁基二甲基硅烷基)氧基]-2-二十六烷酰基氨基-4-十八烷醇 在 10 wt% Pd(OH)2 on carbon 、 四丁基氟化铵 、 氢气 、 silver perchlorate 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 生成 RCAI-61
  参考文献：
  名称：

  RCAI-61 and related 6′-modified analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce interferon-γ in vivo

  摘要：

  We synthesized ten new analogs of 6'-modified KRN7000 (A): RCAI-58, 61, 64, 83, 85-87, 113, 119, and 125. They could be synthesized by alpha-selective galactosylation of ceramide 9 with the 6-modified D-galactopyranosyl fluorides (8a-8f) or L-arabinopyranosyl fluoride (17), or by etherification of the known alcohol 19. Bioassay of the ten analogs demonstrated that RCAI-61 (1, 6'-O-methylated analog of A) was the most potent immunostimulant among them, and could induce the production of a large amount of IFN-gamma even at a low concentration in mice in vivo. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.028

文献信息

• NOVEL alpha-GALACTOSYL CERAMIDE ANALOGS AND USES THEREOF
  申请人：Chang Gung Memorial Hospital, Linkou

  公开号：US20160115188A1

  公开（公告）日：2016-04-28

  The present invention is directed to compounds of formula (I) and pharmaceutical compositions comprising compounds of formula (I) and pharmaceutically acceptable carriers. The invention further comprises improved process for the preparation of compounds of formula (I), and the use of compound of formula (I) to induce a specific immune response or to treat an autoimmune disease.

  本发明涉及化合物的公式(I)以及包含公式(I)化合物和药用载体的药物组合物。该发明还涉及改进的用于制备公式(I)化合物的方法，以及利用公式(I)化合物诱导特定免疫反应或治疗自身免疫疾病的用途。
• RCAI-61, the 6′-O-methylated analog of KRN7000: its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo
  作者：Takuya Tashiro、Ryusuke Nakagawa、Sayo Inoue、Masao Shiozaki、Hiroshi Watarai、Masaru Taniguchi、Kenji Mori

  DOI：10.1016/j.tetlet.2008.09.074

  日期：2008.11

  RCAI-61, the 6'-O-methylated analog of KRN7000, and six other analogs with modified 6'-position of the galactose moiety of KRN7000 were synthesized to examine their bioactivity for mouse lymphocytes. Methyl alpha-D-galactopyranoside was the starting material for RCAI-58, 61, 64, 83, 85, and 86, while RCAI-87 was prepared from methyl beta-L-arabinopyranoside. Bioassay showed RCAI-61 to be a Much more potent stimulant of mouse lymphocytes than KRN7000 and RCAI-56 to induce the production of a large amount of IFN-gamma in vivo. (C) 2008 Elsevier Ltd. All rights reserved.
• NOVEL GLYCOLIPID AND USE THEREOF
  申请人：Riken

  公开号：EP2272854B1

  公开（公告）日：2015-08-05