N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl]-2-hydroxy-5-iodo-benzamide | 945992-32-5

• 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-dihydro-1H-isoquinolin-2-yl)-butyl]-2-hydroxy-5-iodo-benzamide
• 英文别名: N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-hydroxy-5-iodobenzamide；N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)butyl]-2-hydroxy-5-iodobenzamide
• CAS: 945992-32-5
• 化学式: C₂₂H₂₇IN₂O₄
• 分子量: 510.372
• InChiKey: YWJCFXPUVNVVQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  71
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl]-2-hydroxy-5-iodo-benzamide 、 2-溴乙基乙酸酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 48.0h， 生成 2-[2-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)butylcarbamoyl]-4-iodophenoxy]ethyl acetate
  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
• 作为产物：
  描述：

  5-碘水杨酸 、 4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butan-1-amine 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以27%的产率得到N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl]-2-hydroxy-5-iodo-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

文献信息

• PEGYLATED FLUOROBENZAMIDE ANALOGUES, THEIR SYNTHESIS AND USE IN DIAGNOSTIC IMAGING
  申请人：Mach Robert H.

  公开号：US20120171119A1

  公开（公告）日：2012-07-05

  Pegylated fluoroalkoxybenzamide compounds which selectively bind Sigma-2 receptors are disclosed. These compounds, when labeled with a positron-emitting radioisotope such as 18 F, can be used as radiotracers for medical imaging such as imaging of tumors by positron emission tomography (PET). In addition, these compounds, when labeled 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.

  揭示了选择性结合Sigma-2受体的聚乙二醇化氟烷氧基苯酰胺化合物。这些化合物，当与正电子发射放射性同位素如18F标记时，可用作医学成像的放射示踪剂，例如通过正电子发射断层扫描（PET）成像肿瘤。此外，这些化合物，当与123I标记时，可用作单光子发射计算机断层扫描（SPECT）成像肿瘤的放射示踪剂。还揭示了合成这些化合物的方法。
• 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。
• Radiolabelled fluorobenzamide analogues, their synthesis and use in diagnostic imaging
  申请人：Washington University

  公开号：US08193360B2

  公开（公告）日：2012-06-05

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

  公开了一种选择性结合Sigma-2受体的氟烷氧基苯甲酰胺化合物。这些化合物与18F标记后，可用作正电子发射断层扫描（PET）成像肿瘤的放射性示踪剂。此外，这些化合物标记为123I后，可用作单光子发射计算机断层扫描（SPECT）成像肿瘤的放射性示踪剂。还公开了合成这些化合物的方法。
• US7659400B2
  申请人：——

  公开号：US7659400B2

  公开（公告）日：2010-02-09