1-pentacosyne | 61847-85-6

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 1-pentacosyne
• 英文别名: pentacos-1-yne；Pentacos-1-in
• CAS: 61847-85-6
• 化学式: C₂₅H₄₈
• 分子量: 348.656
• InChiKey: PSVIFCMEORUFBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  55°C
• 沸点：
  402.97°C (estimate)
• 密度：
  0.8383 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  25
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-2-azido-3,4-di-O-para-methoxybenzyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-octadecane 、 1-pentacosyne 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 以72%的产率得到1-((2S,3S,4R)-3,4-bis(4-methoxybenzyloxy)-1-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yloxy)octadecan-2-yl)-4-tricosyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis and Evaluation of 1,2,3-Triazole Containing Analogues of the Immunostimulant α-GalCer

  摘要：

  alpha-GalCer is the first defined and most potent agonistic antigen of the T cell receptor of natural killer T cells. We have prepared a series of 1,2,3-triazole-containing alpha-GalCer analogues in which the lipid chain lengths have been incrementally varied. We found that this isosteric replacement of alpha-GalCer's amide moiety with triazole increases the IL-4 versus IFN-gamma bias of released cytokines. The stimulatory effect was influenced by the length of the attached chain. In particular, the long-chained triazole analogues have a comparable stimulatory effect on cytokine production as alpha-GalCer and exhibit a stronger Th2 cytokine response.

  DOI：

  10.1021/jm061243q

文献信息

• Synthesis and Evaluation of 1,2,3-Triazole Containing Analogues of the Immunostimulant α-GalCer
  作者：Taeho Lee、Minjae Cho、Sung-Youl Ko、Hyun-Jun Youn、Dong Jae Baek、Won-Jea Cho、Chang-Yuil Kang、Sanghee Kim

  DOI：10.1021/jm061243q

  日期：2007.2.8

  alpha-GalCer is the first defined and most potent agonistic antigen of the T cell receptor of natural killer T cells. We have prepared a series of 1,2,3-triazole-containing alpha-GalCer analogues in which the lipid chain lengths have been incrementally varied. We found that this isosteric replacement of alpha-GalCer's amide moiety with triazole increases the IL-4 versus IFN-gamma bias of released cytokines. The stimulatory effect was influenced by the length of the attached chain. In particular, the long-chained triazole analogues have a comparable stimulatory effect on cytokine production as alpha-GalCer and exhibit a stronger Th2 cytokine response.