1-hexacosyne | 61847-86-7

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 1-hexacosyne
• 英文别名: hexacosyne；hexacos-1-yne；Hexacos-1-in
• CAS: 61847-86-7
• 化学式: C₂₆H₅₀
• 分子量: 362.683
• InChiKey: XJOQNDHCYRZZBQ-UHFFFAOYSA-N

物化性质

• 熔点：
  57°C
• 沸点：
  414.23°C (estimate)
• 密度：
  0.8408 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  13.3
• 重原子数：
  26
• 可旋转键数：
  22
• 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-hexacosyne 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-tetracosyl-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

• Phase transfer agent assisted biphasic CuAAC reaction
  作者：Jae Hyun Kim、Sanghee Kim

  DOI：10.1039/c4ra03356f

  日期：——

  phase transfer agent assisted biphasic Cu(I) catalyzed azide–alkyne 1,3-dipolar cycloaddition (CuAAC) reaction system was developed. A biphasic reaction medium consisting of water and an organic solvent ensures the dissolution of reagents and substrates. Tris(triazolylmethyl)amine ligands with an appropriate hydrophilic–lipophilic balance are able to extract copper from the aqueous phase to the organic

  开发了一种相转移剂辅助的双相Cu（I）催化的叠氮化物-炔烃1,3-偶极环加成（CuAAC）反应系统。由水和有机溶剂组成的双相反应介质可确保试剂和底物的溶解。具有适当亲水-亲脂平衡的三（三唑基甲基）胺配体能够将铜从水相萃取到有机相，从而加快CuAAC反应速率。本系统广泛适用于具有各种功能的底物，包括游离氨基，尤其是亲脂底物。
• 알파-갈락토실세라마이드 유사체, 이의 제조방법 및 이를 포함하는 면역조절 이상으로 인한 질환의 치료 또는 예방용 약학적 조성물
  申请人：Spark Biopharma, Inc (주)스파크바이오파마(120160160632) Corp. No ▼ 110111-5956482BRN ▼441-88-00285

  公开号：KR101969129B1

  公开（公告）日：2019-04-15

  본 발명은 알파-갈락토실세라마이드 유사체, 이의 제조방법 및 이를 포함하는 면역조절 이상으로 인한 질환의 치료 또는 예방용 약학적 조성물에 관한 것으로, 더욱 상세하게는 NKT 세포 내 Th1 또는 Th2 반응의 선택적인 활성화를 유도할 수 있어 면역조절 이상으로 인한 질환의 치료 또는 예방에 효과적인 알파-갈락토실세라마이드 유사체, 이의 제조방법 및 이를 포함하는 면역조절 이상으로 인한 질환의 치료 또는 예방용 약학적 조성물에 관한 것이다.

  本发明涉及一种α-半乳甘露糖鞘氨醇类似物，其制备方法以及包含在免疫调节异常引起的疾病的治疗或预防药学组合物中，更详细地说，可以诱导NKT细胞内Th1或Th2反应的选择性激活，从而对免疫调节异常引起的疾病的治疗或预防具有有效作用的α-半乳甘露糖鞘氨醇类似物，其制备方法以及包含在免疫调节异常引起的疾病的治疗或预防用药学组合物。
• Design, synthesis, and preliminary biological evaluation of a novel triazole analogue of ceramide
  作者：Sanghee Kim、Minjae Cho、Taeho Lee、Sukjin Lee、Hye-Young Min、Sang Kook Lee

  DOI：10.1016/j.bmcl.2007.05.086

  日期：2007.8

  The amide bond of ceramide was replaced by the non-hydrolyzable 1,2,3-triazole functionality. Click chemistry was employed for synthesis of the designed analogues. Our preliminary biological evaluation indicated that the amide moiety of ceramide is amenable to bioisosteric substitution with the triazole moiety. Some of the analogues were more potent than C2-ceramide as cytotoxic agents, and the observed

  神经酰胺的酰胺键被不可水解的1,2,3-三唑官能团取代。点击化学用于设计类似物的合成。我们的初步生物学评估表明，神经酰胺的酰胺部分适合用三唑部分进行生物等位取代。一些类似物作为细胞毒性剂比C2-神经酰胺更有效，并且观察到的细胞毒性可能是通过诱导细胞凋亡来介导的。
• 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.