(1-benzyl-7-trimethylstannanyl-1H-quinolin-4-ylidene)-pentyl-amine | 1450909-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (1-benzyl-7-trimethylstannanyl-1H-quinolin-4-ylidene)-pentyl-amine
• 英文别名: 1-benzyl-N-pentyl-7-trimethylstannyl-4H-quinolin-4-amine
• CAS: 1450909-21-3
• 化学式: C₂₄H₃₄N₂Sn
• 分子量: 469.257
• InChiKey: ATTCURAAOWMQNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1-benzyl-7-trimethylstannanyl-1H-quinolin-4-ylidene)-pentyl-amine 在 盐酸 、 sodium iodide 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 生成 1-benzyl-7-(125I)iodanyl-N-pentyl-4H-quinolin-4-amine
  参考文献：
  名称：

  Synthesis and evaluation of a 125I-labeled iminodihydroquinoline-derived tracer for imaging of voltage-gated sodium channels

  摘要：

  In vivo imaging of voltage-gated sodium channels (VGSCs) can potentially provide insights into the activation of neuronal pathways and aid the diagnosis of a number of neurological diseases. The iminodihydroquinoline WIN17317-3 is one of the most potent sodium channel blockers reported to date and binds with high affinity to VGSCs throughout the rat brain. We have synthesized a I-125-labeled analogue of WIN17317-3 and evaluated the potential of the tracer for imaging of VGSCs with SPEC. Automated patch clamp studies with CHO cells expressing the Na(v)1.2 isoform and displacement studies with [H-3]BTX yielded comparable results for the non-radioactive iodinated iminodihydroquinoline and WIN17317-3. However, the I-125-labeled tracer was rapidly metabolized in vivo, and suffered from low brain uptake and high accumulation of radioactivity in the intestines. The results suggest that iminodihydroquinolines are poorly suited for tracer development. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.014
• 作为产物：
  描述：

  4-氯-7-碘喹啉 在 四(三苯基膦)钯 、 sodium iodide 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 30.5h， 生成 (1-benzyl-7-trimethylstannanyl-1H-quinolin-4-ylidene)-pentyl-amine
  参考文献：
  名称：

  Synthesis and evaluation of a 125I-labeled iminodihydroquinoline-derived tracer for imaging of voltage-gated sodium channels

  摘要：

  In vivo imaging of voltage-gated sodium channels (VGSCs) can potentially provide insights into the activation of neuronal pathways and aid the diagnosis of a number of neurological diseases. The iminodihydroquinoline WIN17317-3 is one of the most potent sodium channel blockers reported to date and binds with high affinity to VGSCs throughout the rat brain. We have synthesized a I-125-labeled analogue of WIN17317-3 and evaluated the potential of the tracer for imaging of VGSCs with SPEC. Automated patch clamp studies with CHO cells expressing the Na(v)1.2 isoform and displacement studies with [H-3]BTX yielded comparable results for the non-radioactive iodinated iminodihydroquinoline and WIN17317-3. However, the I-125-labeled tracer was rapidly metabolized in vivo, and suffered from low brain uptake and high accumulation of radioactivity in the intestines. The results suggest that iminodihydroquinolines are poorly suited for tracer development. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.014

文献信息

• Synthesis and evaluation of a 125I-labeled iminodihydroquinoline-derived tracer for imaging of voltage-gated sodium channels
  作者：Carlos Pérez-Medina、Niral Patel、Mathew Robson、Mark F. Lythgoe、Erik Årstad

  DOI：10.1016/j.bmcl.2013.07.014

  日期：2013.9

  In vivo imaging of voltage-gated sodium channels (VGSCs) can potentially provide insights into the activation of neuronal pathways and aid the diagnosis of a number of neurological diseases. The iminodihydroquinoline WIN17317-3 is one of the most potent sodium channel blockers reported to date and binds with high affinity to VGSCs throughout the rat brain. We have synthesized a I-125-labeled analogue of WIN17317-3 and evaluated the potential of the tracer for imaging of VGSCs with SPEC. Automated patch clamp studies with CHO cells expressing the Na(v)1.2 isoform and displacement studies with [H-3]BTX yielded comparable results for the non-radioactive iodinated iminodihydroquinoline and WIN17317-3. However, the I-125-labeled tracer was rapidly metabolized in vivo, and suffered from low brain uptake and high accumulation of radioactivity in the intestines. The results suggest that iminodihydroquinolines are poorly suited for tracer development. (C) 2013 Elsevier Ltd. All rights reserved.