4-(4-((4-phenylpiperazin-1-yl)methyl)-1H-1,2,3-triazol-1-yl)aniline | 1224470-96-5

• 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: 4-(4-((4-phenylpiperazin-1-yl)methyl)-1H-1,2,3-triazol-1-yl)aniline
• CAS: 1224470-96-5
• 化学式: C₁₉H₂₂N₆
• 分子量: 334.424
• InChiKey: ONJHPATUNQZMNW-UHFFFAOYSA-N

物化性质

• 熔点：
  157 °C
• 沸点：
  551.4±60.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  4-(4-((4-phenylpiperazin-1-yl)methyl)-1H-1,2,3-triazol-1-yl)aniline 、 乙酸酐 反应 0.75h， 以92%的产率得到N-(4-(4-((4-phenylpiperazin-1-yl)methyl)-1H-1,2,3-triazol-1-yl)phenyl)acetamide
  参考文献：
  名称：

  Searching for multi-target antipsychotics: Discovery of orally active heterocyclic N-phenylpiperazine ligands of D2-like and 5-HT1A receptors

  摘要：

  We described herein the design, synthesis, and pharmacological evaluation of N-phenylpiperazine heterocyclic derivatives as multi-target compounds potentially useful for the treatment of schizophrenia. The isosteric replacement of the heterocyclic ring at the biaryl motif generating pyrazole, 1,2,3-triazole, and 2-methylimidazole[1,2-a]pyridine derivatives resulted in 21 analogues with different substitutions at the para-biaryl and para-phenylpiperazine positions. Among the compounds prepared, 4 (LASSBio-579) and 10 (LASSBio-664) exhibited an adequate binding profile and a potential for schizophrenia positive symptoms treatment without cataleptogenic effects. Structural features of this molecular scaffold are discussed regarding binding affinity and selectivity for D-2-like, 5-HT1A, and 5-HT2A receptors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.040
• 作为产物：
  描述：

  1-{[1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl]methyl}-4-phenylpiperazine 在 palladium 10% on activated carbon 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以96%的产率得到4-(4-((4-phenylpiperazin-1-yl)methyl)-1H-1,2,3-triazol-1-yl)aniline
  参考文献：
  名称：

  Searching for multi-target antipsychotics: Discovery of orally active heterocyclic N-phenylpiperazine ligands of D2-like and 5-HT1A receptors

  摘要：

  We described herein the design, synthesis, and pharmacological evaluation of N-phenylpiperazine heterocyclic derivatives as multi-target compounds potentially useful for the treatment of schizophrenia. The isosteric replacement of the heterocyclic ring at the biaryl motif generating pyrazole, 1,2,3-triazole, and 2-methylimidazole[1,2-a]pyridine derivatives resulted in 21 analogues with different substitutions at the para-biaryl and para-phenylpiperazine positions. Among the compounds prepared, 4 (LASSBio-579) and 10 (LASSBio-664) exhibited an adequate binding profile and a potential for schizophrenia positive symptoms treatment without cataleptogenic effects. Structural features of this molecular scaffold are discussed regarding binding affinity and selectivity for D-2-like, 5-HT1A, and 5-HT2A receptors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.040