2-(3-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)propyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-1(2H)-one | 103936-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(3-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)propyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-1(2H)-one
• 英文别名: 2-[3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-propyl]-6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one；1-<1-Oxo-6,7-dimethoxy-1,2,3,4-tetrahydro-isochinolinyl-(2)>-3-<6,7-dimethoxy-1,2,3,4-tetrahydro-isochinolinyl-(2)>-propan；2-[3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)propyl]-6,7-dimethoxy-3,4-dihydroisoquinolin-1-one
• CAS: 103936-91-0
• 化学式: C₂₅H₃₂N₂O₅
• 分子量: 440.539
• InChiKey: WMABPBDYDMOPQK-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200 °C
• 沸点：
  636.0±55.0 °C(predicted)
• 密度：
  1.167±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6,7-二甲氧基-3,4-二氢-异喹啉-1-酮 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.17h， 生成 2-(3-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)propyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-1(2H)-one
  参考文献：
  名称：

  Development of 3,4-dihydroisoquinolin-1(2H)-one derivatives for the Positron Emission Tomography (PET) imaging of σ2 receptors

  摘要：

  sigma(2) Receptors are promising biomarkers for cancer diagnosis given the relationship between the proliferative status of tumors and their density. With the aim of contributing to the research of sigma(2) receptor Positron Emission Tomography (PET) probes, we developed 243-16,7-dimethoxy-3,4dihydroisoquinolin-2(1H)-yllpropy11-3,4-dihydroisoquinolin-1(2H)-one (3), with optimal sigma(2) pharmacological properties and appropriate lipophilicity. Hence, 3 served as the lead compound for the development of a series of dihydroisoquinolinones amenable to radiolabeling. Radiosynthesis for compound 26, which displayed the most appropriate sigma(2) profile, was developed and sigma(2) specific binding for the corresponding [18F1-26 was confirmed by in vitro autoradiography on rat brain slices. Despite the excellent in vitro properties, [189-26 could not successfully image sigma(2) receptors in the rat brain in vivo, maybe because of its interaction with P-gp. Nevertheless, [189-26 may still be worthy of further investigation for the imaging of sigma(2) receptors in peripheral tumors devoid of P-gp overexpression. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.018

文献信息

• Development of 3,4-dihydroisoquinolin-1(2H)-one derivatives for the Positron Emission Tomography (PET) imaging of σ2 receptors
  作者：Carmen Abate、Svetlana V. Selivanova、Adrienne Müller、Stefanie D. Krämer、Roger Schibli、Roberta Marottoli、Roberto Perrone、Francesco Berardi、Mauro Niso、Simon M. Ametamey

  DOI：10.1016/j.ejmech.2013.09.018

  日期：2013.11

  sigma(2) Receptors are promising biomarkers for cancer diagnosis given the relationship between the proliferative status of tumors and their density. With the aim of contributing to the research of sigma(2) receptor Positron Emission Tomography (PET) probes, we developed 243-16,7-dimethoxy-3,4dihydroisoquinolin-2(1H)-yllpropy11-3,4-dihydroisoquinolin-1(2H)-one (3), with optimal sigma(2) pharmacological properties and appropriate lipophilicity. Hence, 3 served as the lead compound for the development of a series of dihydroisoquinolinones amenable to radiolabeling. Radiosynthesis for compound 26, which displayed the most appropriate sigma(2) profile, was developed and sigma(2) specific binding for the corresponding [18F1-26 was confirmed by in vitro autoradiography on rat brain slices. Despite the excellent in vitro properties, [189-26 could not successfully image sigma(2) receptors in the rat brain in vivo, maybe because of its interaction with P-gp. Nevertheless, [189-26 may still be worthy of further investigation for the imaging of sigma(2) receptors in peripheral tumors devoid of P-gp overexpression. (C) 2013 Elsevier Masson SAS. All rights reserved.