1-N,3-N,5-N-tris(3-aminopropyl)benzene-1,3,5-tricarboxamide | 1104610-49-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-N,3-N,5-N-tris(3-aminopropyl)benzene-1,3,5-tricarboxamide
• CAS: 1104610-49-2
• 化学式: C₁₈H₃₀N₆O₃
• 分子量: 378.475
• InChiKey: OSBDKAHBOKOYHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  165
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-N,3-N,5-N-tris(3-aminopropyl)benzene-1,3,5-tricarboxamide 、 1,1-双(二乙氧基磷酰基)乙烯 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Bisphosphonate sequestering agents. Synthesis and preliminary evaluation for in vitro and in vivo uranium(VI) chelation

  摘要：

  A library of bisphosphonate-based ligands was prepared using solution-phase parallel synthesis and tested for its uranium-binding properties. With the help of a screening method, based on a chromophoric complex displacement procedure, 23 dipodal and tripodal chelates bearing bisphosphonate chelating functions were found to display very high affinity for the uranyl ion and were selected for evaluation of their in vivo uranyl-removal efficacy. Among them, 11 ligands induced a huge modification of the uranyl biodistribution by deviating the metal from kidney and bones to liver. Among the other ligands, the most potent was the dipodal bisphosphonate 3C which reduced the retention of uranyl and increased its excretion by around 10% of the injected metal. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.01.018
• 作为产物：
  描述：

  三甲基1,3,5-苯三羟酸酯 、 1,3-丙二胺 以 甲醇 为溶剂， 反应 12.0h， 以98%的产率得到1-N,3-N,5-N-tris(3-aminopropyl)benzene-1,3,5-tricarboxamide
  参考文献：
  名称：

  Bisphosphonate sequestering agents. Synthesis and preliminary evaluation for in vitro and in vivo uranium(VI) chelation

  摘要：

  A library of bisphosphonate-based ligands was prepared using solution-phase parallel synthesis and tested for its uranium-binding properties. With the help of a screening method, based on a chromophoric complex displacement procedure, 23 dipodal and tripodal chelates bearing bisphosphonate chelating functions were found to display very high affinity for the uranyl ion and were selected for evaluation of their in vivo uranyl-removal efficacy. Among them, 11 ligands induced a huge modification of the uranyl biodistribution by deviating the metal from kidney and bones to liver. Among the other ligands, the most potent was the dipodal bisphosphonate 3C which reduced the retention of uranyl and increased its excretion by around 10% of the injected metal. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.01.018

文献信息

• Fatty aldehyde bisulfite adducts as a purification handle in ionizable lipid synthesis
  作者：Graham Atwood、Sona Purbiya、Cassandra Reid、Brandon Smith、Kuljit Kaur、Drew Wicks、Peter Gaudet、K. Cory MacLeod、Jean-Francois Vincent-Rocan

  DOI：10.1039/d4ra05189k

  日期：——

  allowing for a more scalable synthesis. Impurities were removed by formation of this fatty aldehyde bisulfite adduct at the penultimate step and by performing the final reductive amination directly with the fatty aldehyde bisulfite adduct. This eliminates chromatographic separations for all prepared aldehyde containing intermediates. Along with ALC-0315, FTT5 and SM-102 ionizable lipids were prepared

  ALC-0315是辉瑞新冠疫苗配方的关键成分，通过在氧化步骤后采用固体加合物形成和过滤代替标准色谱分离，可以快速获得ALC-0315，从而实现更大规模的合成。通过在倒数第二步形成该脂肪醛亚硫酸氢盐加合物并通过直接用脂肪醛亚硫酸氢盐加合物进行最终的还原胺化来除去杂质。这消除了所有制备的含醛中间体的色谱分离。利用该策略与 ALC-0315、FTT5 和 SM-102 可电离脂质一起制备。这项工作为更可持续地获取这些关键的可电离脂质铺平了道路，这将降低未来世界重要疫苗和药物供应的风险。