2-[4-(2-pyridyl)piperazine-1-yl]-N-[4-(2-methylthiazol-4-yl)phenyl]acetamide

• 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: 2-[4-(2-pyridyl)piperazine-1-yl]-N-[4-(2-methylthiazol-4-yl)phenyl]acetamide
• 英文别名: 2-[4-(2-Pyridyl)piperazine-1-yl]-N-[4-(2-methylthiazol-4-yl)phenyl]acetamide (5n)；N-[4-(2-methyl-1,3-thiazol-4-yl)phenyl]-2-(4-pyridin-2-ylpiperazin-1-yl)acetamide
• 化学式: C₂₁H₂₃N₅OS
• 分子量: 393.513
• InChiKey: RJWDUYBGHNYPLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  89.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(2-甲基-1,3-噻唑-4-基)苯胺 在 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 2.0h， 生成 2-[4-(2-pyridyl)piperazine-1-yl]-N-[4-(2-methylthiazol-4-yl)phenyl]acetamide
  参考文献：
  名称：

  Design, synthesis and evaluation of new thiazole-piperazines as acetylcholinesterase inhibitors

  摘要：

  In this study, some new 2-(4-substituted piperazine-1-yl)-N-[4-(2-methylthiazol-4-yl)phenyl]acetamide derivatives were synthesized. The synthesized compounds were screened for their anticholinesterase activity on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes by in vitro Ellman's method. The structural elucidation of the compounds was performed by using IR, H-1-NMR, C-13-NMR and FAB(+)-MS spectral data and elemental analyses results. Biological assays revealed that at 0.1 mu M concentration, the most active compounds against AChE were 5n, 5o and 5p that indicated 96.44, 99.83 and 89.70% inhibition rates, respectively. Besides, IC50 value of the compound 5o was determined as 0.011 mu M, whereas IC50 value of standard drug donepezil was 0.054 mu M. The synthesized compounds did not show any notable inhibitory activity against BChE.

  DOI：

  10.3109/14756366.2012.709242

文献信息

• Design, synthesis and evaluation of new thiazole-piperazines as acetylcholinesterase inhibitors
  作者：Leyla Yurttaş、Zafer Asım Kaplancıklı、Yusuf Özkay

  DOI：10.3109/14756366.2012.709242

  日期：2013.10.1

  In this study, some new 2-(4-substituted piperazine-1-yl)-N-[4-(2-methylthiazol-4-yl)phenyl]acetamide derivatives were synthesized. The synthesized compounds were screened for their anticholinesterase activity on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes by in vitro Ellman's method. The structural elucidation of the compounds was performed by using IR, H-1-NMR, C-13-NMR and FAB(+)-MS spectral data and elemental analyses results. Biological assays revealed that at 0.1 mu M concentration, the most active compounds against AChE were 5n, 5o and 5p that indicated 96.44, 99.83 and 89.70% inhibition rates, respectively. Besides, IC50 value of the compound 5o was determined as 0.011 mu M, whereas IC50 value of standard drug donepezil was 0.054 mu M. The synthesized compounds did not show any notable inhibitory activity against BChE.