4,5,6,7-Tetrachloro-3'-hydroxy-2',4',5',7'-tetraiodo-6'-methoxyspiro[2-benzofuran-3,9'-xanthene]-1-one | 118584-84-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4,5,6,7-Tetrachloro-3'-hydroxy-2',4',5',7'-tetraiodo-6'-methoxyspiro[2-benzofuran-3,9'-xanthene]-1-one
• CAS: 118584-84-2
• 化学式: C₂₁H₆Cl₄I₄O₅
• 分子量: 987.706
• InChiKey: QGBCFWJWWFCWSP-UHFFFAOYSA-N

物化性质

• 沸点：
  809.3±65.0 °C(Predicted)
• 密度：
  2.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5,6,7-Tetrachloro-3'-hydroxy-2',4',5',7'-tetraiodo-6'-methoxyspiro[2-benzofuran-3,9'-xanthene]-1-one 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以42.6%的产率得到4,5,6,7-tetrachloro-2',4',5',7'-tetraiodo-3',6'-dimethoxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one
  参考文献：
  名称：

  Rose Bengal analogs and vesicular glutamate transporters (VGLUTs)

  摘要：

  Vesicular glutamate transporters (VGLUTs) allow the loading of presynaptic glutamate vesicles and thus play a critical role in glutamatergic synaptic transmission. Rose Bengal (RB) is the most potent known VGLUT inhibitor (K-i 25 nM); therefore we designed, synthesized and tested in brain preparations, a series of analogs based on this scaffold. We showed that among the two tautomers of RB, the carboxylic and not the lactonic form is active against VGLUTs and generated a pharmacophore model to determine the minimal structure requirements. We also tested RB specificity in other neurotransmitter uptake systems. RB proved to potently inhibit VMAT (K-i 64 nM) but weakly VACHT (K-i > 9.7 mu M) and may be a useful tool in glutamate/acetylcholine co-transmission studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.069
• 作为产物：
  描述：

  孟加拉红内酯 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以24%的产率得到4,5,6,7-Tetrachloro-3'-hydroxy-2',4',5',7'-tetraiodo-6'-methoxyspiro[2-benzofuran-3,9'-xanthene]-1-one
  参考文献：
  名称：

  Rose Bengal analogs and vesicular glutamate transporters (VGLUTs)

  摘要：

  Vesicular glutamate transporters (VGLUTs) allow the loading of presynaptic glutamate vesicles and thus play a critical role in glutamatergic synaptic transmission. Rose Bengal (RB) is the most potent known VGLUT inhibitor (K-i 25 nM); therefore we designed, synthesized and tested in brain preparations, a series of analogs based on this scaffold. We showed that among the two tautomers of RB, the carboxylic and not the lactonic form is active against VGLUTs and generated a pharmacophore model to determine the minimal structure requirements. We also tested RB specificity in other neurotransmitter uptake systems. RB proved to potently inhibit VMAT (K-i 64 nM) but weakly VACHT (K-i > 9.7 mu M) and may be a useful tool in glutamate/acetylcholine co-transmission studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.069