(1RS,11SR)-3,6,9,15-tetraazabicyclo[9.3.1]pentadecane | 883242-27-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1RS,11SR)-3,6,9,15-tetraazabicyclo[9.3.1]pentadecane
• 英文别名: (1S,11R)-3,6,9,15-tetrazabicyclo[9.3.1]pentadecane
• CAS: 883242-27-1
• 化学式: C₁₁H₂₄N₄
• 分子量: 212.338
• InChiKey: JNXIYBRZFRDOPM-PHIMTYICSA-N

物化性质

• 沸点：
  334.9±10.0 °C(Predicted)
• 密度：
  0.918±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  48.1
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1RS,11SR)-3,6,9,15-tetraazabicyclo[9.3.1]pentadecane 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 40.0h， 生成 2-[(1R,11S)-3,9,15-tris(carboxymethyl)-3,6,9,15-tetrazabicyclo[9.3.1]pentadecan-6-yl]acetic acid
  参考文献：
  名称：

  Synthesis and Evaluation of Novel Macrocyclic and Acyclic Ligands as Contrast Enhancement Agents for Magnetic Resonance Imaging

  摘要：

  Novel chelates PIP-DTPA, AZEP-DTPA, NETA, NPTA, and PIP-DOTA were synthesized and evaluated as potential magnetic resonance imaging (MRI) contrast enhancement agents. The T-1 and T-2 relaxivities of their corresponding Gd(III) complexes are reported. At clinically relevant field strengths, the relaxivities of the complexes are comparable to that of the clinically used contrast agents Gd(DTPA) and Gd(DOTA). The serum stability of the Gd-153-labeled complexes, Gd(PIP-DTPA), Gd(AZEP-DTPA), Gd(PIP-DOTA), Gd(NETA), and Gd(NPTA), was assessed by measuring the release of Gd-153 from the complexes. Gd-153(NETA), Gd-153(PIP-DTPA), and Gd-153(PIP-DOTA) were found to be stable in human serum for up to 14 days without any measurable loss of radioactivity. Significant release of Gd-153 was observed with the Gd-153(III) radiolabled NPTA. In vivo biodistribution of the Gd-153-labeled complexes was performed to evaluate their in vivo stability. While Gd(AZEP-DTPA) and Gd(NPTA) were found to be unstable in vivo, Gd(NETA), Gd(PIP-DTPA), and Gd(PIP-DOTA) were excreted without dissociation. These results suggest that the Gd(III) complexes of the novel chelates NETA, PIP-DTPA, and PIP-DOTA possess potential as MRI contrast enhancement agents. In particular, the piperidine backboned chelates Gd(PIP-DTPA) and Gd(PIP-DOTA) displayed reduced kidney retention as compared to the nonspecific MRI contrast agent Gd(DOTA) at all time points, although the observed effects were relatively small at 0.5 h postinjection. Incorporation of the lipophilic piperidine ring appears to confer a moderate effect on the liver uptake of these two chelates.

  DOI：

  10.1021/jm051009k
• 作为产物：
  描述：

  cis-2,6-piperidinedicarboxylic acid 在 palladium on activated charcoal sodium hydroxide 、 dimethyl sulfide borane 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、206.84 kPa 条件下， 反应 183.0h， 生成 (1RS,11SR)-3,6,9,15-tetraazabicyclo[9.3.1]pentadecane
  参考文献：
  名称：

  Synthesis and Evaluation of Novel Macrocyclic and Acyclic Ligands as Contrast Enhancement Agents for Magnetic Resonance Imaging

  摘要：

  Novel chelates PIP-DTPA, AZEP-DTPA, NETA, NPTA, and PIP-DOTA were synthesized and evaluated as potential magnetic resonance imaging (MRI) contrast enhancement agents. The T-1 and T-2 relaxivities of their corresponding Gd(III) complexes are reported. At clinically relevant field strengths, the relaxivities of the complexes are comparable to that of the clinically used contrast agents Gd(DTPA) and Gd(DOTA). The serum stability of the Gd-153-labeled complexes, Gd(PIP-DTPA), Gd(AZEP-DTPA), Gd(PIP-DOTA), Gd(NETA), and Gd(NPTA), was assessed by measuring the release of Gd-153 from the complexes. Gd-153(NETA), Gd-153(PIP-DTPA), and Gd-153(PIP-DOTA) were found to be stable in human serum for up to 14 days without any measurable loss of radioactivity. Significant release of Gd-153 was observed with the Gd-153(III) radiolabled NPTA. In vivo biodistribution of the Gd-153-labeled complexes was performed to evaluate their in vivo stability. While Gd(AZEP-DTPA) and Gd(NPTA) were found to be unstable in vivo, Gd(NETA), Gd(PIP-DTPA), and Gd(PIP-DOTA) were excreted without dissociation. These results suggest that the Gd(III) complexes of the novel chelates NETA, PIP-DTPA, and PIP-DOTA possess potential as MRI contrast enhancement agents. In particular, the piperidine backboned chelates Gd(PIP-DTPA) and Gd(PIP-DOTA) displayed reduced kidney retention as compared to the nonspecific MRI contrast agent Gd(DOTA) at all time points, although the observed effects were relatively small at 0.5 h postinjection. Incorporation of the lipophilic piperidine ring appears to confer a moderate effect on the liver uptake of these two chelates.

  DOI：

  10.1021/jm051009k