(2S,3S,4R)-1-O-(6-deoxy-6-(4-phenyltriazol-1-yl)-α-D-galactopyranosyl)-2-hexacosylaminooctadecane-1,3,4-triol | 1383455-79-5

• 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,3S,4R)-1-O-(6-deoxy-6-(4-phenyltriazol-1-yl)-α-D-galactopyranosyl)-2-hexacosylaminooctadecane-1,3,4-triol
• 英文别名: N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[(4-phenyltriazol-1-yl)methyl]oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide
• CAS: 1383455-79-5
• 化学式: C₅₈H₁₀₄N₄O₈
• 分子量: 985.486
• InChiKey: NYCUGMSRDIIMCZ-RUIMKTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.2
• 重原子数：
  70
• 可旋转键数：
  46
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 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)-3,4-di-O-benzyl-1-O-(2,3,4-tri-O-benzyl-6-deoxy-6-(4-phenyltriazol-1-yl)-α-D-galactopyranosyl)-2-hexacosylaminooctadecane-1,3,4-triol 在 氢气 、 钯 作用下， 以 乙醇 、 氯仿 为溶剂， 以40%的产率得到(2S,3S,4R)-1-O-(6-deoxy-6-(4-phenyltriazol-1-yl)-α-D-galactopyranosyl)-2-hexacosylaminooctadecane-1,3,4-triol
  参考文献：
  名称：

  Synthesis of 6″-triazole-substituted α-GalCer analogues as potent iNKT cell stimulating ligands

  摘要：

  We report the synthesis of a small series of 6 ''-triazol-1-yl-substituted alpha-GalCer analogues by late-stage conversion of the 6 ''-OH to an azide group, copper-catalyzed azide-alkyne cycloaddition and final deprotection. When evaluated for their capacity to induce IL-2 secretion in vitro, all compounds proved equally potent or superior to alpha-GalCer. The S. A. R suggests that the improved antigenic activity is mainly triggered by the triazole functionalization in se. While the introduction of selected substitutuents at C-4 of this heterocyclic ring is tolerated, this generally fails to further improve antigenicity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.063

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.
• Synthesis of 6″-triazole-substituted α-GalCer analogues as potent iNKT cell stimulating ligands
  作者：Nora Pauwels、Sandrine Aspeslagh、Dirk Elewaut、Serge Van Calenbergh

  DOI：10.1016/j.bmc.2012.09.063

  日期：2012.12

  We report the synthesis of a small series of 6 ''-triazol-1-yl-substituted alpha-GalCer analogues by late-stage conversion of the 6 ''-OH to an azide group, copper-catalyzed azide-alkyne cycloaddition and final deprotection. When evaluated for their capacity to induce IL-2 secretion in vitro, all compounds proved equally potent or superior to alpha-GalCer. The S. A. R suggests that the improved antigenic activity is mainly triggered by the triazole functionalization in se. While the introduction of selected substitutuents at C-4 of this heterocyclic ring is tolerated, this generally fails to further improve antigenicity. (C) 2012 Elsevier Ltd. All rights reserved.