1-(3,4,5-三甲氧基苯基)-哌嗪盐酸盐 | 38869-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-(3,4,5-三甲氧基苯基)-哌嗪盐酸盐
• 英文名称: 1-(3,4,5-Trimethoxy-phenyl)-piperazine; hydrochloride
• 英文别名: 1-(3,4,5-Trimethoxyphenyl)piperazine hydrochloride；1-(3,4,5-trimethoxyphenyl)piperazine;hydrochloride
• CAS: 38869-07-7
• 化学式: C₁₃H₂₀N₂O₃*ClH
• 分子量: 288.774
• InChiKey: UWWBIYGLDJXNGY-UHFFFAOYSA-N

物化性质

• 熔点：
  210°C (dec.)

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  43
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  、 1-(3,4,5-三甲氧基苯基)-哌嗪盐酸盐 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 5-Methoxy-3-{4-[4-(3,4,5-trimethoxy-phenyl)-piperazin-1-yl]-butyl}-1H-indole
  参考文献：
  名称：

  Indolebutylamines as Selective 5-HT_1A Agonists

  摘要：

  A series of new 1-[4-(indol-3-yl)butyl]-4-arylpiperazines was prepared to identify highly selective and potent 5-HT1A agonists as potential pharmacological tools in studies of mood disorders. The combination of structural elements (indole-alkyl-amine and aryl-piperazine) known to introduce 5-HT1A receptor affinity and the proper selection of substituents (R on the indole moiety and R' on the aryl moiety) led to compounds with high receptor specificity and affinity. In particular, the introduction of the methyl ether or the unsubstituted carboxamide as substituents in position 5 of the indole (R) guaranteed serotonergic 5-HT1A affinity compared to the unsubstituted analogue. Para-substituted arylpiperazines (R') decreased dopaminergic D-2 binding and increased selectivity for the 5-HT1A receptor. Agonistic 5-HT1A receptor activity was confirmed in vivo in the ultrasonic vocalization test, and the results suggest that the introduction of the carboxamide residue leads to better bioavailability than the corresponding methyl ether. 3-{4-[4-(4-Carbamoylphenyl)piperazin-1-yl}butyl}-1H-indole-5-carboxamide 54 was identified as a highly selective 5-HT1A receptor agonist [GTPgammaS, ED50 = 4.7 nM] with nanomolar 5-HT1A affinity [IC50 = 0.9 nM] and selectivity [D-2, IC50 > 850 nM]. 3-{4-[4-(4-Methoxyphenyl)piperazin-1-yl]butyl}-1H-indole-5-carboxamide 45 is one of the most potent and selective 5-HT1A agonists known [5-HT1A, IC50 = 0.09 nM; D-2, IC50 = 140 nM].

  DOI：

  10.1021/jm040792y