(5R,9R,11E)-5-(4-methoxyphenylmethylidenylamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one | 923272-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (5R,9R,11E)-5-(4-methoxyphenylmethylidenylamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one
• 英文别名: (1R,9R,13E)-13-ethylidene-1-[(4-methoxyphenyl)methylideneamino]-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,10-trien-5-one
• CAS: 923272-94-0
• 化学式: C₂₃H₂₄N₂O₂
• 分子量: 360.456
• InChiKey: NQSMOKKBRJAZEE-DNAOVAILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  石杉碱甲 、 4-甲氧基苯甲醛 在 三乙胺 作用下， 以 甲醇 为溶剂， 以80%的产率得到(5R,9R,11E)-5-(4-methoxyphenylmethylidenylamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one
  参考文献：
  名称：

  Rational design and synthesis of highly potent anti-acetylcholinesterase activity huperzine A derivatives

  摘要：

  By targeting multi-active sites of acetylcholinesterase (AChE), a series of huperzine A (Hup A) derivatives with various aromatic ring groups were designed and synthesized by Schiff reaction. They were evaluated as AChE and butyrylcholinesterase (BChE) inhibitors. Results showed very significant specificity that the group of imine derivatives could inhibit TcAChE and hAChE, but no inhibitory effect on hBChE was detected. The experiment was explained by a docking study. In the docking model, we confirmed that aromatic ring of Hup A derivatives played the pi-pi stacking against aminophenol residues of AChE, and the structure-activity relationship (SAR) was discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.017

文献信息

• Rational design and synthesis of highly potent anti-acetylcholinesterase activity huperzine A derivatives
  作者：Jian Yan、Lirong Sun、Guisheng Wu、Ping Yi、Fumei Yang、Lin Zhou、Xianmin Zhang、Zhongrong Li、Xiaosheng Yang、Huairong Luo、Minghua Qiu

  DOI：10.1016/j.bmc.2009.08.017

  日期：2009.10

  By targeting multi-active sites of acetylcholinesterase (AChE), a series of huperzine A (Hup A) derivatives with various aromatic ring groups were designed and synthesized by Schiff reaction. They were evaluated as AChE and butyrylcholinesterase (BChE) inhibitors. Results showed very significant specificity that the group of imine derivatives could inhibit TcAChE and hAChE, but no inhibitory effect on hBChE was detected. The experiment was explained by a docking study. In the docking model, we confirmed that aromatic ring of Hup A derivatives played the pi-pi stacking against aminophenol residues of AChE, and the structure-activity relationship (SAR) was discussed. (C) 2009 Elsevier Ltd. All rights reserved.