1-butyl-4-[4-(dimethylamino)phenyl]pyridinium bromide | 39873-66-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-butyl-4-[4-(dimethylamino)phenyl]pyridinium bromide
• CAS: 39873-66-0
• 化学式: Br*C₁₇H₂₃N₂
• 分子量: 335.287
• InChiKey: MVWSZPUOSXGSML-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.51
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  7.12
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  正溴丁烷 、 N,N-二甲基-4-(4-吡啶基)苯胺 以 甲苯 为溶剂， 反应 24.0h， 以52%的产率得到1-butyl-4-[4-(dimethylamino)phenyl]pyridinium bromide
  参考文献：
  名称：

  Binding-Induced Fluorescence of Serotonin Transporter Ligands: A Spectroscopic and Structural Study of 4-(4-(Dimethylamino)phenyl)-1-methylpyridinium (APP⁺) and APP⁺ Analogues

  摘要：

  The binding-induced fluorescence of 4-(4-(dimethy- lamino)-phenyl)-1-methylpyridinium (APP(+)) and two new serotonin transporter (SERT)-binding fluorescent analogues, 1-butyl-4-[4-(1-dimethylamino)phenyl]-pyridinium bromide (BPP+) and 1-methyl-4-[4-(1-piperidinyl)phenyl]-pyridinium (PPP+), has been investigated. Optical spectroscopy reveals that these probes are highly sensitive to their chemical microenvironment, responding to variations in polarity with changes in transition energies and responding to changes in viscosity or rotational freedom with emission enhancements. Molecular docking calculations reveal that the probes are able to access the nonpolar and conformationally restrictive binding pocket of SERT. As a result, the probes exhibit previously not identified binding-induced turn-on emission that is spectroscopically distinct from dyes that have accumulated intracellularly. Thus, binding and transport dynamics of SERT ligands can be resolved both spatially and spectroscopically.

  DOI：

  10.1021/cn400230x