ethyl 2-(2',7'-dibromo-6'-hydroxy-4',5'-dinitro-3'-oxo-3H-xanthen-9'-yl)benzoate | 1253821-19-0

• 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: ethyl 2-(2',7'-dibromo-6'-hydroxy-4',5'-dinitro-3'-oxo-3H-xanthen-9'-yl)benzoate
• CAS: 1253821-19-0
• 化学式: C₂₂H₁₂Br₂N₂O₉
• 分子量: 608.153
• InChiKey: VSGYIGJSQBQWPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  163.02
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  溴乙烷 、 曙红(醇溶) 在 potassium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以46.7%的产率得到ethyl 2-(2',7'-dibromo-6'-hydroxy-4',5'-dinitro-3'-oxo-3H-xanthen-9'-yl)benzoate
  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