3-Benzo[1,3]dioxol-5-yl-5-(4-benzyloxy-phenyl)-5-hydroxy-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one | 882041-72-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3-Benzo[1,3]dioxol-5-yl-5-(4-benzyloxy-phenyl)-5-hydroxy-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one
• CAS: 882041-72-7
• 化学式: C₃₄H₃₀O₉
• 分子量: 582.607
• InChiKey: CNEFVSDXJYMPRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  43.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  101.91
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3-Benzo[1,3]dioxol-5-yl-5-(4-benzyloxy-phenyl)-5-hydroxy-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 12.0h， 以39%的产率得到PD 169390
  参考文献：
  名称：

  Synthesis, in vitro pharmacology and biodistribution studies of new PD 156707-derived ETA receptor radioligands

  摘要：

  It is assumed that the regulation of cardiac endothelin (ET) receptor density is abnormal in heart diseases. From that perspective, an ET receptor radioligand is needed to assess ET receptor density in vivo. The nonpeptidyl ETA receptor antagonist PD 169390 was labelled with radioiodine to give a putative radioligand for SPECT. Labelling with [I-125]iodide and [I-123]iodide was accomplished with good to excellent radiochemical yields. The affinities of the nonradioactive reference and those of selected precursor compounds for ETA receptors were determined, using [I-125]iodine labelled endothelin-1 with mouse ventricular membranes. All employed substances exhibited potent in vitro pharmacological characteristics with K-i values comparable to that of the lead compound PD 156707. Biodistribution studies and scintigraphic imaging experiments in mice, however, showed no significant uptake of the [I-123] derivative in the heart. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.039
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 2-(benzo[1,3]dioxol-5-yl)-1-(4-benzyloxyphenyl)-4-oxobutyric acid methyl ester 在 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以74%的产率得到3-Benzo[1,3]dioxol-5-yl-5-(4-benzyloxy-phenyl)-5-hydroxy-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one
  参考文献：
  名称：

  Synthesis, in vitro pharmacology and biodistribution studies of new PD 156707-derived ETA receptor radioligands

  摘要：

  It is assumed that the regulation of cardiac endothelin (ET) receptor density is abnormal in heart diseases. From that perspective, an ET receptor radioligand is needed to assess ET receptor density in vivo. The nonpeptidyl ETA receptor antagonist PD 169390 was labelled with radioiodine to give a putative radioligand for SPECT. Labelling with [I-125]iodide and [I-123]iodide was accomplished with good to excellent radiochemical yields. The affinities of the nonradioactive reference and those of selected precursor compounds for ETA receptors were determined, using [I-125]iodine labelled endothelin-1 with mouse ventricular membranes. All employed substances exhibited potent in vitro pharmacological characteristics with K-i values comparable to that of the lead compound PD 156707. Biodistribution studies and scintigraphic imaging experiments in mice, however, showed no significant uptake of the [I-123] derivative in the heart. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.039