N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-(2-fluoroethoxy)-5-iodobenzamide

• 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: N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-(2-fluoroethoxy)-5-iodobenzamide
• 英文别名: N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl]-2-(2-fluoro-ethoxy)-5-iodo-benzamide；N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)butyl]-2-(2-fluoroethoxy)-5-iodobenzamide
• 化学式: C₂₄H₃₀FIN₂O₄
• 分子量: 556.416
• InChiKey: IRFSOVRQSWDTBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  60
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-(2-fluoroethoxy)-5-iodobenzamide 在 copper(l) iodide 、 sodium azide 、 bathophenanthrolinedispufonic acid disodium salt 、 copper(II) sulfate 、 sodium ascorbate 、 N,N'-二甲基乙二胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-5-(4-((dimethylamino)methyl)-1H-1,2,3-triazol-1-yl)-2-(2-fluoroethoxy)benzamide
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationship Studies of Conformationally Flexible Tetrahydroisoquinolinyl Triazole Carboxamide and Triazole Substituted Benzamide Analogues as σ₂ Receptor Ligands

  摘要：

  Two novel classes of compounds targeting the sigma-2 (sigma(2)) receptor were synthesized, and their bioactivities to binding sigma(1) and sigma(2) receptors were measured. Four novel triazole carboxamide analogues, 24d, 24e, 24f, and 39c, demonstrated high affinity and selectivity for the sigma(2) receptor. These data suggest C-11-labeled versions of these compounds may be potential sigma(2)-selective radiotracers for imaging the proliferative status of solid tumors.

  DOI：

  10.1021/jm5001453
• 作为产物：
  描述：

  5-碘水杨酸甲酯 在 sodium hydride 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 mineral oil 为溶剂， 生成 N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-(2-fluoroethoxy)-5-iodobenzamide
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationship Studies of Conformationally Flexible Tetrahydroisoquinolinyl Triazole Carboxamide and Triazole Substituted Benzamide Analogues as σ₂ Receptor Ligands

  摘要：

  Two novel classes of compounds targeting the sigma-2 (sigma(2)) receptor were synthesized, and their bioactivities to binding sigma(1) and sigma(2) receptors were measured. Four novel triazole carboxamide analogues, 24d, 24e, 24f, and 39c, demonstrated high affinity and selectivity for the sigma(2) receptor. These data suggest C-11-labeled versions of these compounds may be potential sigma(2)-selective radiotracers for imaging the proliferative status of solid tumors.

  DOI：

  10.1021/jm5001453

文献信息

• RADIOLABELLED BENZAMIDE ANALOGUES, THEIR SYNTHESIS AND USE IN DIAGNOSTIC IMAGING
  申请人：Mach Robert

  公开号：US20100150836A1

  公开（公告）日：2010-06-17

  Fluoroalkoxybenzamide compounds which selectively bind Sigma-2 receptors are disclosed. These compounds, when labelled with 18 F, can be used as radiotracers for imaging of tumors by positron emission tomography (PET). In addition, these compounds, when labelled with 123 I, can be used as radiotracers for imaging of tumors by single photon emission computed tomography (SPECT). Methods for synthesis of these compounds are also disclosed.

  本文披露了一种选择性结合Sigma-2受体的氟烷氧基苯酰胺化合物。这些化合物与18F标记后，可用于正电子发射断层扫描（PET）成像肿瘤。此外，这些化合物与123I标记后，可用于单光子发射计算机断层扫描（SPECT）成像肿瘤。本文还披露了这些化合物的合成方法。
• RADIOLABELLED FLUOROBENZAMIDE ANALOGUES, THEIR SYNTHESIS AND USE IN DIAGNOSTIC IMAGING
  申请人：Mach Robert H.

  公开号：US20110230662A1

  公开（公告）日：2011-09-22

  Fluoroalkoxybenzamide compounds which selectively bind Sigma-2 receptors are disclosed. These compounds, when labelled with 18 F, can be used as radiotracers for imaging of tumors by positron emission tomography (PET). In addition, these compounds, when labelled with 123 I, can be used as radiotracers for imaging of tumors by single photon emission computed tomography (SPECT). Methods for synthesis of these compounds are also disclosed.

  本发明公开了选择性结合Sigma-2受体的氟烷氧基苯酰胺化合物。这些化合物标记18F后，可作为正电子发射断层扫描（PET）成像肿瘤的放射性示踪剂。此外，这些化合物标记123I后，可作为单光子发射计算机断层扫描（SPECT）成像肿瘤的放射性示踪剂。本发明还公开了这些化合物的合成方法。
• Fluorine-18-Labeled Benzamide Analogues for Imaging the σ₂ Receptor Status of Solid Tumors with Positron Emission Tomography
  作者：Zhude Tu、Jinbin Xu、Lynne A. Jones、Shihong Li、Craig Dumstorff、Suwanna Vangveravong、Delphine L. Chen、Kenneth T. Wheeler、Michael J. Welch、Robert H. Mach

  DOI：10.1021/jm0614883

  日期：2007.7.1

  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.
• US7659400B2
  申请人：——

  公开号：US7659400B2

  公开（公告）日：2010-02-09
• US7947838B2
  申请人：——

  公开号：US7947838B2

  公开（公告）日：2011-05-24