(Z)-4-((7,8-dimethoxy-4-oxoisochroman-3-ylidene)methyl)-1-(3-nitrobenzyl)pyridin-1-ium bromide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (Z)-4-((7,8-dimethoxy-4-oxoisochroman-3-ylidene)methyl)-1-(3-nitrobenzyl)pyridin-1-ium bromide
• 英文别名: (3Z)-7,8-dimethoxy-3-[[1-[(3-nitrophenyl)methyl]pyridin-1-ium-4-yl]methylidene]-1H-isochromen-4-one;bromide
• 化学式: Br*C₂₄H₂₁N₂O₆
• 分子量: 513.345
• InChiKey: BLHPKPOXRHQXBK-BWLGBDCWSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  94.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-bromo-2,3-dimethoxybenzyl alcohol 在 正丁基锂 、 sodium methylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 7.5h， 生成 (Z)-4-((7,8-dimethoxy-4-oxoisochroman-3-ylidene)methyl)-1-(3-nitrobenzyl)pyridin-1-ium bromide
  参考文献：
  名称：

  Design, synthesis, biological evaluation and docking study of 4-isochromanone hybrids bearing N-benzyl pyridinium moiety as dual binding site acetylcholinesterase inhibitors

  摘要：

  A series of novel 4-isochromanone hybrids bearing N-benzyl pyridinium moiety as dual binding site acetylcholinesterase inhibitors have been designed and synthesized. The screening results showed that most of the compounds exhibited potent anti-AChE activity in the range of nM concentrations. The 1-(4-fluorobenzyl) substituted derivative 9d exhibited the most potent anti-AChE activity with IC50 value of 8.9 nM and high AChE/BuChE selectivity (SI > 230). Kinetic and molecular modeling studies suggested that compound 9d was mixed-type inhibitor, binding simultaneously to CAS and PAS of AChE. Besides, the preliminary structure-activity relationships were discussed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.063

文献信息

• Design, synthesis, biological evaluation and docking study of 4-isochromanone hybrids bearing N-benzyl pyridinium moiety as dual binding site acetylcholinesterase inhibitors
  作者：Chaolei Wang、Zheng Wu、Hao Cai、Shengtao Xu、Jie Liu、Jieyun Jiang、Hequan Yao、Xiaoming Wu、Jinyi Xu

  DOI：10.1016/j.bmcl.2015.09.063

  日期：2015.11

  A series of novel 4-isochromanone hybrids bearing N-benzyl pyridinium moiety as dual binding site acetylcholinesterase inhibitors have been designed and synthesized. The screening results showed that most of the compounds exhibited potent anti-AChE activity in the range of nM concentrations. The 1-(4-fluorobenzyl) substituted derivative 9d exhibited the most potent anti-AChE activity with IC50 value of 8.9 nM and high AChE/BuChE selectivity (SI > 230). Kinetic and molecular modeling studies suggested that compound 9d was mixed-type inhibitor, binding simultaneously to CAS and PAS of AChE. Besides, the preliminary structure-activity relationships were discussed. (C) 2015 Elsevier Ltd. All rights reserved.