tert-butyl N-[N'-[2-(4-fluoro-3-hydroxyphenyl)ethyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate | 1426298-32-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: tert-butyl N-[N'-[2-(4-fluoro-3-hydroxyphenyl)ethyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
• CAS: 1426298-32-9
• 化学式: C₁₉H₂₈FN₃O₅
• 分子量: 397.447
• InChiKey: DXYOZJHOMKQJPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[N'-[2-(4-fluoro-3-hydroxyphenyl)ethyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以87%的产率得到(4-fluoro-m-hydroxyphenethyl)guanidine
  参考文献：
  名称：

  Synthesis and bioevaluation of [18F]4-fluoro-m-hydroxyphenethylguanidine ([18F]4F-MHPG): A novel radiotracer for quantitative PET studies of cardiac sympathetic innervation

  摘要：

  A new cardiac sympathetic nerve imaging agent, [F-18]4-fluoro-m-hydroxyphenethylguanidine ([F-18]4F-MHPG), was synthesized and evaluated. The radiosynthetic intermediate [F-18]4-fluoro-m-tyramine ([F-18]4F-MTA) was prepared and then sequentially reacted with cyanogen bromide and NH4Br/NH4OH to afford [F-18]4F-MHPG. Initial bioevaluations of [F-18]4F-MHPG (biodistribution studies in rats and kinetic studies in the isolated rat heart) were similar to results previously reported for the carbon-11 labeled analog [C-11]4F-MHPG. The neuronal uptake rate of [F-18]4F-MHPG into the isolated rat heart was 0.68 ml/min/g wet and its retention time in sympathetic neurons was very long (T-1/2 > 13 h). A PET imaging study in a nonhuman primate with [F-18]4F-MHPG provided high quality images of the heart, with heart-to-blood ratios at 80-90 min after injection of 5-to-1. These initial kinetic and imaging studies of [F-18]4F-MHPG suggest that this radiotracer may allow for more accurate quantification of regional cardiac sympathetic nerve density than is currently possible with existing neuronal imaging agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.106
• 作为产物：
  描述：

  3-benzyloxy-4-fluorobenzyl alcohol 在 硼烷四氢呋喃络合物 、 氢溴酸 、 三溴化磷 、 三乙胺 、 mercury dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 tert-butyl N-[N'-[2-(4-fluoro-3-hydroxyphenyl)ethyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
  参考文献：
  名称：

  Synthesis and bioevaluation of [18F]4-fluoro-m-hydroxyphenethylguanidine ([18F]4F-MHPG): A novel radiotracer for quantitative PET studies of cardiac sympathetic innervation

  摘要：

  A new cardiac sympathetic nerve imaging agent, [F-18]4-fluoro-m-hydroxyphenethylguanidine ([F-18]4F-MHPG), was synthesized and evaluated. The radiosynthetic intermediate [F-18]4-fluoro-m-tyramine ([F-18]4F-MTA) was prepared and then sequentially reacted with cyanogen bromide and NH4Br/NH4OH to afford [F-18]4F-MHPG. Initial bioevaluations of [F-18]4F-MHPG (biodistribution studies in rats and kinetic studies in the isolated rat heart) were similar to results previously reported for the carbon-11 labeled analog [C-11]4F-MHPG. The neuronal uptake rate of [F-18]4F-MHPG into the isolated rat heart was 0.68 ml/min/g wet and its retention time in sympathetic neurons was very long (T-1/2 > 13 h). A PET imaging study in a nonhuman primate with [F-18]4F-MHPG provided high quality images of the heart, with heart-to-blood ratios at 80-90 min after injection of 5-to-1. These initial kinetic and imaging studies of [F-18]4F-MHPG suggest that this radiotracer may allow for more accurate quantification of regional cardiac sympathetic nerve density than is currently possible with existing neuronal imaging agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.106

文献信息

• Synthesis and bioevaluation of [18F]4-fluoro-m-hydroxyphenethylguanidine ([18F]4F-MHPG): A novel radiotracer for quantitative PET studies of cardiac sympathetic innervation
  作者：Keun Sam Jang、Yong-Woon Jung、Phillip S. Sherman、Carole A. Quesada、Guie Gu、David M. Raffel

  DOI：10.1016/j.bmcl.2013.01.106

  日期：2013.3

  A new cardiac sympathetic nerve imaging agent, [F-18]4-fluoro-m-hydroxyphenethylguanidine ([F-18]4F-MHPG), was synthesized and evaluated. The radiosynthetic intermediate [F-18]4-fluoro-m-tyramine ([F-18]4F-MTA) was prepared and then sequentially reacted with cyanogen bromide and NH4Br/NH4OH to afford [F-18]4F-MHPG. Initial bioevaluations of [F-18]4F-MHPG (biodistribution studies in rats and kinetic studies in the isolated rat heart) were similar to results previously reported for the carbon-11 labeled analog [C-11]4F-MHPG. The neuronal uptake rate of [F-18]4F-MHPG into the isolated rat heart was 0.68 ml/min/g wet and its retention time in sympathetic neurons was very long (T-1/2 > 13 h). A PET imaging study in a nonhuman primate with [F-18]4F-MHPG provided high quality images of the heart, with heart-to-blood ratios at 80-90 min after injection of 5-to-1. These initial kinetic and imaging studies of [F-18]4F-MHPG suggest that this radiotracer may allow for more accurate quantification of regional cardiac sympathetic nerve density than is currently possible with existing neuronal imaging agents. (C) 2013 Elsevier Ltd. All rights reserved.