(E)-1-(5-carboxypentyl)-2-(2-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)vinyl)-3,3-dimethyl-3H-indol-1-ium bromide | 1258655-02-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (E)-1-(5-carboxypentyl)-2-(2-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)vinyl)-3,3-dimethyl-3H-indol-1-ium bromide
• CAS: 1258655-02-5
• 化学式: Br*C₃₁H₃₇N₂O₄
• 分子量: 581.55
• InChiKey: USMZALPGZJGQPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  73.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N,N'-二琥珀酰亚胺基碳酸酯 、 (E)-1-(5-carboxypentyl)-2-(2-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)vinyl)-3,3-dimethyl-3H-indol-1-ium bromide 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以68%的产率得到(E)-2-[2-(7-diethylamino-2-oxo-2H-chromen-3-yl)vinyl]-3,3-dimethyl-1-[6-(2,5-dioxopyrrolidin-1-yl)-6-oxohexyl]indolium bromide
  参考文献：
  名称：

  Novel Derivatives of 1-Cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine (PB28) with Improved Fluorescent and σ Receptors Binding Properties

  摘要：

  Despite the promising potentials of sigma(2) receptors in cancer therapy and diagnosis, there are still ambiguities related to the nature and physiological role of the a, protein. With the aim of providing potent and reliable tools to be used in sigma(2) receptor research, we developed a novel series of fluorescent sigma(2) ligands on the basis of our previous work, where high-affinity sigma(2) ligand 1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-n-propyl]piperazine (1, PB28) was used as the pharmacophore. Compared to the previous compounds, these novel ligands displayed improved fluorescence and a, binding properties, were sigma(2)-specifically taken up by breast tumor cells, and were successfully employed in confocal microscopy. Compound 14, which was the best compromise between pharmacological and fluorescent properties, was successfully employed in flow cytometry, demonstrating its potential to be used as a tool in nonradioactive binding assays for studying the affinity of putative sigma(2) receptor ligands.

  DOI：

  10.1021/jm401874n
• 作为产物：
  描述：

  6-(2,3,3-三甲基吲哚-1-鎓-1-基)己酸溴化物 、 2H-1-苯并吡喃-3-羧醛, 7-(二乙基氨基)-2-氧代- 在 乙酸酐 作用下， 反应 4.0h， 以70%的产率得到(E)-1-(5-carboxypentyl)-2-(2-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)vinyl)-3,3-dimethyl-3H-indol-1-ium bromide
  参考文献：
  名称：

  Identification of a red-emitting fluorescent ligand for in vitro visualization of human serotonin 5-HT1A receptors

  摘要：

  The 5-HT1A receptor subtype is the most thoroughly studied serotonin receptor subtype. We report here the design, synthesis and characterization of two new fluorescent ligands for the 5-HT1A receptor. The new 1-arylpiperazine-based red-emitting fluorescent compound 6 displayed good binding affinity at the 5-HT1A receptor (K-i = 35 nM) and was able to label specifically the human 5-HT1A receptor stably expressed in CHO cells visualized using confocal laser scanning microscopy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.027