(S)-3-{1-(4-fluorophenyl)-5-[5-(2-fluorophenyl)-4H-1,2,4-triazol-3-yl]-1,3-dihydroisobenzofuran-1-yl}-N,N-dimethylpropan-1-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3-{1-(4-fluorophenyl)-5-[5-(2-fluorophenyl)-4H-1,2,4-triazol-3-yl]-1,3-dihydroisobenzofuran-1-yl}-N,N-dimethylpropan-1-amine
• 英文别名: 3-[(1S)-1-(4-fluorophenyl)-5-[5-(2-fluorophenyl)-1H-1,2,4-triazol-3-yl]-3H-2-benzofuran-1-yl]-N,N-dimethylpropan-1-amine
• 化学式: C₂₇H₂₆F₂N₄O
• 分子量: 460.526
• InChiKey: HTUVXWIELTWJPX-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  邻氟苯甲酸乙酯 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 水 、 正丁醇 为溶剂， 生成 (S)-3-{1-(4-fluorophenyl)-5-[5-(2-fluorophenyl)-4H-1,2,4-triazol-3-yl]-1,3-dihydroisobenzofuran-1-yl}-N,N-dimethylpropan-1-amine
  参考文献：
  名称：

  Synthesis of novel triazoles and a tetrazole of escitalopram as cholinesterase inhibitors

  摘要：

  A novel serie of escitalopram triazoles (60-88) and a tetrazole (89) have been synthesized and subjected to a study to establish the inhibitory potential of these compounds toward acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Some selectivity in inhibition has been observed. The 4-chlorophenyl- (75, IC50, 6.71 +/- 0.25 mu M) and 2-methylphenyl-(70, IC50, 9.52 +/- 0.23 mu M) escitalopram triazole derivatives depicted high AChE inhibition, while 2-fluorophenyl-(76, IC50 = 4.52 +/- 0.17 mu M) and 4-fluorophenyl-(78, IC50 = 5.31 +/- 0.43 mu M) have found to be excellent BChE inhibitors. It has also been observed that ortho, meta and para substituted electron donating groups increase the inhibition, while electron withdrawing groups reduce the inhibition. Docking analyses of inhibitors with AChE have depicted the binding energies for 70 and 75 as Delta G(bind) -6.42 and -6.93 kcal/mol, respectively, while ligands 76 and 78 have shown the binding affinity Delta G(bind) -9.04 and -8.51 kcal/mol, respectively, for BChE. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.051

文献信息

• Synthesis of novel triazoles and a tetrazole of escitalopram as cholinesterase inhibitors
  作者：Mehr-un-Nisa、Munawar A. Munawar、Fauzia A. Chattha、Samina Kousar、Jawaria Munir、Tayaba Ismail、Muhammad Ashraf、Misbahul A. Khan

  DOI：10.1016/j.bmc.2015.06.051

  日期：2015.9

  A novel serie of escitalopram triazoles (60-88) and a tetrazole (89) have been synthesized and subjected to a study to establish the inhibitory potential of these compounds toward acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Some selectivity in inhibition has been observed. The 4-chlorophenyl- (75, IC50, 6.71 +/- 0.25 mu M) and 2-methylphenyl-(70, IC50, 9.52 +/- 0.23 mu M) escitalopram triazole derivatives depicted high AChE inhibition, while 2-fluorophenyl-(76, IC50 = 4.52 +/- 0.17 mu M) and 4-fluorophenyl-(78, IC50 = 5.31 +/- 0.43 mu M) have found to be excellent BChE inhibitors. It has also been observed that ortho, meta and para substituted electron donating groups increase the inhibition, while electron withdrawing groups reduce the inhibition. Docking analyses of inhibitors with AChE have depicted the binding energies for 70 and 75 as Delta G(bind) -6.42 and -6.93 kcal/mol, respectively, while ligands 76 and 78 have shown the binding affinity Delta G(bind) -9.04 and -8.51 kcal/mol, respectively, for BChE. (C) 2015 Elsevier Ltd. All rights reserved.