(+/-)1-[1-methyl-2-(3-nitro-4-aminophenyl)ethyl]-4-phenylpiperazine | 431946-49-5

• 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: (+/-)1-[1-methyl-2-(3-nitro-4-aminophenyl)ethyl]-4-phenylpiperazine
• 英文别名: 2-nitro-4-[2-(4-phenylpiperazin-1-yl)propyl]aniline
• CAS: 431946-49-5
• 化学式: C₁₉H₂₄N₄O₂
• 分子量: 340.425
• InChiKey: HLLFLFLEVDAVKC-UHFFFAOYSA-N

物化性质

• 沸点：
  523.5±50.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  75.64
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+/-)1-[1-methyl-2-(3-nitro-4-aminophenyl)ethyl]-4-phenylpiperazine 在 Ra-Ni 盐酸 、 一水合肼 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 1.5h， 生成 6-[2-(4-Phenyl-piperazin-1-yl)-propyl]-1,4-dihydro-quinoxaline-2,3-dione
  参考文献：
  名称：

  Introduction of a methyl group in α- or β-position of 1-heteroarylethyl-4-phenyl-piperazines affects their dopaminergic/serotonergic properties

  摘要：

  1-(2-Heteroarylalkyl)-4-phenylpiperazines containing methyl group in either the alpha- or the beta-position of the side alkyl chain were synthesized as racemic mixtures. 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 nucleus and hippocampus, respectively, as a source of the corresponding receptors. 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. None of the new compounds expressed significant affinity for the D-1 receptor. Introduction of the methyl group into the beta-position of the parent molecules increased the affinity for the D-2 receptor (10b-13b), and decreased the affinity for the 5-HT1A receptor with the exception of imidazole (11b) which was a rather efficient displacer of 8-OH-DPAT. Most potent of the newly synthesized compounds in [H-3]spiperone assay were compounds (+/-)6-[1-methyl-2-(4-phenylpiperazin-n-1-yl)-ethyl]-1, 4-dihydroquinoxaline-2,3-dione (10b), K-d = 6.0 nM and (+/-)5-[1-methyl-2-(4-phenylpiperazin-1-yl)-ethyl]-1,3-dihydrobenzoirnidazol-2-thione (13b), K-d = 5.3 nM. However, compounds containing methyl group in alpha-position (10a-13a) of the parent molecules expressed a decreased affinity for the D-2 receptor, while the affinity for the 5-HT1A receptor remained in the same range of concentrations as that of closely related achiral parent compounds (14-17) run in the same binding assays as references.

  DOI：

  10.1002/1521-4184(200112)334:12<375::aid-ardp375>3.0.co;2-p
• 作为产物：
  描述：

  N-苯基哌嗪 在 Ra-Ni 盐酸 、 硫酸 、 硝酸 、 sodium cyanoborohydride 、 一水合肼 、 zinc(II) chloride 作用下， 以 甲醇 、 乙醇 、 乙酸酐 、 1,2-二氯乙烷 为溶剂， 反应 34.0h， 生成 (+/-)1-[1-methyl-2-(3-nitro-4-aminophenyl)ethyl]-4-phenylpiperazine
  参考文献：
  名称：

  Introduction of a methyl group in α- or β-position of 1-heteroarylethyl-4-phenyl-piperazines affects their dopaminergic/serotonergic properties

  摘要：

  1-(2-Heteroarylalkyl)-4-phenylpiperazines containing methyl group in either the alpha- or the beta-position of the side alkyl chain were synthesized as racemic mixtures. 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 nucleus and hippocampus, respectively, as a source of the corresponding receptors. 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. None of the new compounds expressed significant affinity for the D-1 receptor. Introduction of the methyl group into the beta-position of the parent molecules increased the affinity for the D-2 receptor (10b-13b), and decreased the affinity for the 5-HT1A receptor with the exception of imidazole (11b) which was a rather efficient displacer of 8-OH-DPAT. Most potent of the newly synthesized compounds in [H-3]spiperone assay were compounds (+/-)6-[1-methyl-2-(4-phenylpiperazin-n-1-yl)-ethyl]-1, 4-dihydroquinoxaline-2,3-dione (10b), K-d = 6.0 nM and (+/-)5-[1-methyl-2-(4-phenylpiperazin-1-yl)-ethyl]-1,3-dihydrobenzoirnidazol-2-thione (13b), K-d = 5.3 nM. However, compounds containing methyl group in alpha-position (10a-13a) of the parent molecules expressed a decreased affinity for the D-2 receptor, while the affinity for the 5-HT1A receptor remained in the same range of concentrations as that of closely related achiral parent compounds (14-17) run in the same binding assays as references.

  DOI：

  10.1002/1521-4184(200112)334:12<375::aid-ardp375>3.0.co;2-p