[18F]-N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl]-2-(2-fluoro-ethoxy)-5-methyl-benzamide | 945992-47-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: [18F]-N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl]-2-(2-fluoro-ethoxy)-5-methyl-benzamide
• 英文别名: N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-(2-[18F]fluoroethoxy)-5-methylbenzamide；Benzamide, N-(4-(3,4-dihydro-6,7-dimethoxy-2(1H)-isoquinolinyl)butyl)-2-(2-(fluoro-18F)ethoxy)-5-methyl-；N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)butyl]-2-(2-(18F)fluoranylethoxy)-5-methylbenzamide
• CAS: 945992-47-2
• 化学式: C₂₅H₃₃FN₂O₄
• 分子量: 443.548
• InChiKey: QVRVXSZKCXFBTE-KPVNRNJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  60
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(2-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butylcarbamoyl)-4-methylphenoxy)ethyl methanesulfonate 在 potassium carbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 0.01h， 生成 [18F]-N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl]-2-(2-fluoro-ethoxy)-5-methyl-benzamide
  参考文献：
  名称：

  Fluorine-18-Labeled Benzamide Analogues for Imaging the σ₂ Receptor Status of Solid Tumors with Positron Emission Tomography

  摘要：

  A series of fluorine-containing benzamide analogs was synthesized and evaluated as candidate ligands for positron emission tomography (PET) imaging of the sigma-2 (sigma(2)) receptor status of solid tumors. Four compounds having a moderate to high affinity for sigma(2) receptors and a moderate to low affinity for sigma-1 (sigma(1)) receptors were radiolabeled with fluorine-18 via displacement of the corresponding mesylate precursor with [F-18]fluoride. Biodistribution studies in female Balb/c mice bearing EMT-6 tumor allografts demonstrated that all four F-18-labeled compounds had a high tumor uptake (2.5-3.7% ID/g) and acceptable tumor/normal tissue ratios at 1 and 2 h post-i.v. injection. An analysis of the chemistry and biodistribution data suggested that N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-(2-[F-18]-fluoroethoxy)-5-methylbenzamide ([F-18]3c) and N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-(2-[F-18]-fluoroethoxy)-5-iodo-3-methoxybenzamide ([F-18]3f) are acceptable compounds for imaging the sigma(2) receptor status of solid tumors.

  DOI：

  10.1021/jm0614883