4-{2-[2-(4-biphenylylmethyl)-5-benzimidazolyl]ethyl}-1-phenylpiperazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-{2-[2-(4-biphenylylmethyl)-5-benzimidazolyl]ethyl}-1-phenylpiperazine
• 英文别名: 2-[(4-phenylphenyl)methyl]-6-[2-(4-phenylpiperazin-1-yl)ethyl]-1H-benzimidazole
• 化学式: C₃₂H₃₂N₄
• 分子量: 472.633
• InChiKey: MRKZVSFNMDIOAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-联苯乙酸 、 4-[2-(4-Phenylpiperazin-1-yl)ethyl]benzene-1,2-diamine 在 盐酸 作用下， 反应 6.0h， 生成 4-{2-[2-(4-biphenylylmethyl)-5-benzimidazolyl]ethyl}-1-phenylpiperazine
  参考文献：
  名称：

  Mixed Dopaminergic/Serotonergic Properties of Several 2-Substituted 4-[2-(5-Benzimidazole)ethyl]-1-arylpiperazines

  摘要：

  A series of substituted 4-[2-(5-benzimidazole)ethyl]-arylpiperazines was synthesized by introducing different substituents into position 2 of benzimidazole ring of 4-[2-(N,N-di-n-propylamino)ethyl]-1,2-diaminobenzenes. They were evaluated for in vitro binding affinity at the D-1 and D-2 dopamine and 5-HT1A serotonin receptors using synaptosomal membranes of the bovine caudate nuclei and hippocampi, respectively. Tritiated SCH 23390 (D-1 receptor-selective), spiperone (D-2 receptor selective) and 8-OH-DPAT (5-HT1A receptor selective) were employed as the radioligands. Only compound 6 expressed a moderate binding affinity at the dopamine D-1 receptor, while the remaining ligands were inefficient or weak competitors of [H-3]SCH 23390. Compound 12 was an absolutely inactive competitor of all three radioligands. Also, compound 7 was an inefficient displacer of [H-3]-8-OH-DPAT. Compound 19 with a K-i value of 3.5 nM was the most potent competitor of [H-3]spiperone and compound 13 (K-i = 3.3 nM) was the most efficient in displacing [H-3]-8-OH-DPAT from the 5-HT1A serotonin receptor. Ligands 5, 6, 8-11, and 13-20 expressed mixed dopaminergic/serotonergic activity in nanomolar range of concentrations with varying affinity ratios which strongly depended on the properties of the substituents introduced into position 2 of benzimidazole ring of the parent compounds.

  DOI：

  10.1002/(sici)1521-4184(199801)331:1<22::aid-ardp22>3.0.co;2-q

文献信息

• Mixed Dopaminergic/Serotonergic Properties of Several 2-Substituted 4-[2-(5-Benzimidazole)ethyl]-1-arylpiperazines
  作者：Sladjana Kostic-Rajacic、Vukic Šoškic、Jelena Joksimovic

  DOI：10.1002/(sici)1521-4184(199801)331:1<22::aid-ardp22>3.0.co;2-q

  日期：1998.1

  A series of substituted 4-[2-(5-benzimidazole)ethyl]-arylpiperazines was synthesized by introducing different substituents into position 2 of benzimidazole ring of 4-[2-(N,N-di-n-propylamino)ethyl]-1,2-diaminobenzenes. They were evaluated for in vitro binding affinity at the D-1 and D-2 dopamine and 5-HT1A serotonin receptors using synaptosomal membranes of the bovine caudate nuclei and hippocampi, respectively. Tritiated SCH 23390 (D-1 receptor-selective), spiperone (D-2 receptor selective) and 8-OH-DPAT (5-HT1A receptor selective) were employed as the radioligands. Only compound 6 expressed a moderate binding affinity at the dopamine D-1 receptor, while the remaining ligands were inefficient or weak competitors of [H-3]SCH 23390. Compound 12 was an absolutely inactive competitor of all three radioligands. Also, compound 7 was an inefficient displacer of [H-3]-8-OH-DPAT. Compound 19 with a K-i value of 3.5 nM was the most potent competitor of [H-3]spiperone and compound 13 (K-i = 3.3 nM) was the most efficient in displacing [H-3]-8-OH-DPAT from the 5-HT1A serotonin receptor. Ligands 5, 6, 8-11, and 13-20 expressed mixed dopaminergic/serotonergic activity in nanomolar range of concentrations with varying affinity ratios which strongly depended on the properties of the substituents introduced into position 2 of benzimidazole ring of the parent compounds.