N-(4-(4-((4-phenylpiperazin-1-yl)methyl)-1H-1,2,3-triazol-1-yl)phenyl)acetamide | 1224470-78-3

• 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: N-(4-(4-((4-phenylpiperazin-1-yl)methyl)-1H-1,2,3-triazol-1-yl)phenyl)acetamide
• 英文别名: 4-[4-(4-Phenylpiperazinilmetil)-1H-1,2,3-triazol-4-yl]acetamide；N-[4-[4-[(4-phenylpiperazin-1-yl)methyl]triazol-1-yl]phenyl]acetamide
• CAS: 1224470-78-3
• 化学式: C₂₁H₂₄N₆O
• 分子量: 376.461
• InChiKey: CPFQNXKICZNUDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  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