4,11-N,N'-bis(carbo-tert-butoxymethyl)-16-(4-nitrobenzyl)-1,4,8,11-tetraazabicyclo[6.6.3]heptadecane | 1276543-48-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4,11-N,N'-bis(carbo-tert-butoxymethyl)-16-(4-nitrobenzyl)-1,4,8,11-tetraazabicyclo[6.6.3]heptadecane
• 英文别名: 4,11-bis(carbo-tert-butoxymethyl)-16-(4-nitrobenzyl)-1,4,8,11-tetraazabicyclo[6.6.3]heptadecane；4,11-Bis-(carbo-tert-butoxymethyl)-16-(4-nitrobenzyl)-1,4,8,11-tetraazabicyclo[6.6.3]heptadecane；tert-butyl 2-[11-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-16-[(4-nitrophenyl)methyl]-1,4,8,11-tetrazabicyclo[6.6.3]heptadecan-4-yl]acetate
• CAS: 1276543-48-6
• 化学式: C₃₂H₅₃N₅O₆
• 分子量: 603.803
• InChiKey: TTXNXTXWLAPIJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4,11-N,N'-bis(carbo-tert-butoxymethyl)-16-(4-nitrobenzyl)-1,4,8,11-tetraazabicyclo[6.6.3]heptadecane 在 钯 氢气 、 乙醇 、 乙醚 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以to provide an off-white solid 27 (3.93 g, 97% yield)的产率得到4,11-bis(carbo-tert-butoxymethyl)-16-(4-aminobenzyl)-1,4,8,11-tetraazabicyclo[6.6.3]heptadecane
  参考文献：
  名称：

  Tetraaza macrocyclic compound, preparation method thereof and use thereof

  摘要：

  提供了一种新结构的交叉桥联四氮杂大环化合物，可用作例如诊断成像对比剂或放射性药物，并提供了制备该化合物的方法。所披露的四氮杂大环化合物能够在较低温度下形成稳定的金属络合物，并且与现有的交叉桥联四氮杂大环化合物相比，易于与生物活性物质或化学活性物质结合。

  公开号：

  US09061078B2
• 作为产物：
  描述：

  1,4,8,11-四氮环[9.3.1.1(4,8)]十六烷 在 水 、 sodium carbonate 、 sodium hydroxide 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 79.0h， 生成 4,11-N,N'-bis(carbo-tert-butoxymethyl)-16-(4-nitrobenzyl)-1,4,8,11-tetraazabicyclo[6.6.3]heptadecane
  参考文献：
  名称：

  Propylene Cross-Bridged Macrocyclic Bifunctional Chelator: A New Design for Facile Bioconjugation and Robust ⁶⁴Cu Complex Stability

  摘要：

  The first macrocyclic bifunctional chelator incorporating propylene cross-bridge was efficiently synthesized from cyclam in seven steps. After the introduction of an extra functional group for facile conjugation onto the propylene cross-bridge, the two carboxylic acid pendants could contribute to strong coordination of Cu(II) ions, leading to a robust Cu complex. The cyclic RGD peptide conjugate of PCB-TE2A-NCS was prepared and successfully radiolabeled with (64)Cu ion. The radiolabeled peptide conjugate was evaluated in vivo through a biodistribution study and animal PET imaging to demonstrate high tumor uptake with low background.

  DOI：

  10.1021/jm500348z

文献信息

• NOVEL TETRAAZA MACROCYCLIC COMPOUND, PREPARATION METHOD THEREOF AND USE THEREOF
  申请人：Yoo Jeong Soo

  公开号：US20120219495A1

  公开（公告）日：2012-08-30

  Provided are a cross-bridged tetraaza macrocyclic compound of a novel structure that can be used, for example, as a contrast agent for diagnostic imaging or a radiopharmaceutical and a method for preparing the same. The disclosed tetraaza macrocyclic compound is able to form a stable metal complex at a lower temperature and allows easy conjugation with a bioactive substance or a chemically active substance, when compared to the existing cross-bridged tetraaza macrocyclic compounds.

  提供的是一种新结构的交桥四氮杂大环化合物，可用作诊断成像的造影剂或放射性药物，以及一种制备该化合物的方法。所披露的四氮杂大环化合物能够在较低温度下形成稳定的金属配合物，并且与生物活性物质或化学活性物质相比，易于共轭。
• NOVEL TETRA-AZA MACROCYCLIC COMPOUND, METHOD FOR PREPARING SAME, AND USE THEREOF
  申请人：Kyungpook National University Industry- Academic Cooperation Foundation

  公开号：EP2476683B1

  公开（公告）日：2019-04-03
• US9061078B2
  申请人：——

  公开号：US9061078B2

  公开（公告）日：2015-06-23
• US9353120B2
  申请人：——

  公开号：US9353120B2

  公开（公告）日：2016-05-31
• Propylene Cross-Bridged Macrocyclic Bifunctional Chelator: A New Design for Facile Bioconjugation and Robust ⁶⁴Cu Complex Stability
  作者：Darpan N. Pandya、Nikunj Bhatt、Gwang Il An、Yeong Su Ha、Nisarg Soni、Hochun Lee、Yong Jin Lee、Jung Young Kim、Woonghee Lee、Heesu Ahn、Jeongsoo Yoo

  DOI：10.1021/jm500348z

  日期：2014.9.11

  The first macrocyclic bifunctional chelator incorporating propylene cross-bridge was efficiently synthesized from cyclam in seven steps. After the introduction of an extra functional group for facile conjugation onto the propylene cross-bridge, the two carboxylic acid pendants could contribute to strong coordination of Cu(II) ions, leading to a robust Cu complex. The cyclic RGD peptide conjugate of PCB-TE2A-NCS was prepared and successfully radiolabeled with (64)Cu ion. The radiolabeled peptide conjugate was evaluated in vivo through a biodistribution study and animal PET imaging to demonstrate high tumor uptake with low background.