N-[(2S,3S,4R)-1-[(2S,3R,4S,5R,6R)-6-[(4,5-diphenyltriazol-1-yl)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3,4-dihydroxyoctadecan-2-yl]hexacosanamide | 1383455-86-4

• 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: N-[(2S,3S,4R)-1-[(2S,3R,4S,5R,6R)-6-[(4,5-diphenyltriazol-1-yl)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3,4-dihydroxyoctadecan-2-yl]hexacosanamide
• CAS: 1383455-86-4
• 化学式: C₆₄H₁₀₈N₄O₈
• 分子量: 1061.58
• InChiKey: RJAAWPVKQHFJKC-RUKSZLDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.9
• 重原子数：
  76
• 可旋转键数：
  47
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  179
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (2S,3S,4R)-1-(6-deoxy-6-azido-α-D-galactopyranosyloxy)-2-hexacosanoylamino-3,4-octadecandiol 、 二苯基乙炔 在 二(三苯基膦)环戊二烯基氯化钌(II) 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以72%的产率得到N-[(2S,3S,4R)-1-[(2S,3R,4S,5R,6R)-6-[(4,5-diphenyltriazol-1-yl)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3,4-dihydroxyoctadecan-2-yl]hexacosanamide
  参考文献：
  名称：

  New CD1d agonists: Synthesis and biological activity of 6″-triazole-substituted α-galactosyl ceramides

  摘要：

  Huisgen [3+2] dipolar cycloaddition of 6 ''-azido-6 ''-deoxy-alpha-galactosyl ceramide 11 with a range of alkynes (or a benzyne precursor) yielded a series of triazole-containing alpha-galactosyl ceramide (alpha-GalCer) analogues in high yield. These alpha-GalCer analogues and the precursor azide 11 were tested for their ability to activate iNKT cells and stimulate IL-2 cytokine secretion in vitro, and IFN-gamma and IL-4 cytokine secretion in vivo. Some of these analogues, specifically 11, 12b, 12f and 13, were more potent IL-2 stimulators than the prototypical CD1d agonist, alpha-GalCer 1. In terms of any cytokine bias, most of the triazole-containing analogues exhibited a small Th2 cytokine-biasing response relative to that shown by alpha-GalCer 1. In contrast, the cycloaddition precursor, namely azide 11, provided a small Th1 cytokine-biasing response. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.009

文献信息

• New CD1d agonists: Synthesis and biological activity of 6″-triazole-substituted α-galactosyl ceramides
  作者：Peter J. Jervis、Lisa M. Graham、Erin L. Foster、Liam R. Cox、Steven A. Porcelli、Gurdyal S. Besra

  DOI：10.1016/j.bmcl.2012.05.009

  日期：2012.7

  Huisgen [3+2] dipolar cycloaddition of 6 ''-azido-6 ''-deoxy-alpha-galactosyl ceramide 11 with a range of alkynes (or a benzyne precursor) yielded a series of triazole-containing alpha-galactosyl ceramide (alpha-GalCer) analogues in high yield. These alpha-GalCer analogues and the precursor azide 11 were tested for their ability to activate iNKT cells and stimulate IL-2 cytokine secretion in vitro, and IFN-gamma and IL-4 cytokine secretion in vivo. Some of these analogues, specifically 11, 12b, 12f and 13, were more potent IL-2 stimulators than the prototypical CD1d agonist, alpha-GalCer 1. In terms of any cytokine bias, most of the triazole-containing analogues exhibited a small Th2 cytokine-biasing response relative to that shown by alpha-GalCer 1. In contrast, the cycloaddition precursor, namely azide 11, provided a small Th1 cytokine-biasing response. (C) 2012 Elsevier Ltd. All rights reserved.