N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[(4-octyltriazol-1-yl)methyl]oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide | 1383455-80-8

• 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)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[(4-octyltriazol-1-yl)methyl]oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide
• CAS: 1383455-80-8
• 化学式: C₆₀H₁₁₆N₄O₈
• 分子量: 1021.6
• InChiKey: SLAOWURKPNQZAT-DBQLOCGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.5
• 重原子数：
  72
• 可旋转键数：
  52
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  1-癸炔 、 (2S,3S,4R)-1-(6-deoxy-6-azido-α-D-galactopyranosyloxy)-2-hexacosanoylamino-3,4-octadecandiol 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 10.0h， 以95%的产率得到N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[(4-octyltriazol-1-yl)methyl]oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide
  参考文献：
  名称：

  迈向多价CD1d配体：同源二聚体α-半乳糖基神经酰胺类似物的合成和生物学活性

  摘要：

  图形概要

  DOI：

  10.1016/j.carres.2012.02.034

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.