9-[Nβ-(3'-(nitrooxy)propyl)-β-aminoethylamino]-1,2,3,4-tetrahydroacridine | 1093131-86-2

• 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: 9-[Nβ-(3'-(nitrooxy)propyl)-β-aminoethylamino]-1,2,3,4-tetrahydroacridine
• 英文别名: 3-[2-(1,2,3,4-Tetrahydroacridin-9-ylamino)ethylamino]propyl nitrate
• CAS: 1093131-86-2
• 化学式: C₁₈H₂₄N₄O₃
• 分子量: 344.414
• InChiKey: UUEALOFRAQKSLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  92
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  9-(2-aminoethylamino)-1,2,3,4-tetrahydroacridine 、 3-bromopropyl nitrate 在 potassium carbonate 、 potassium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以38%的产率得到9-[Nβ-(3'-(nitrooxy)propyl)-β-aminoethylamino]-1,2,3,4-tetrahydroacridine
  参考文献：
  名称：

  NO-Donating Tacrine Hybrid Compounds Improve Scopolamine-Induced Cognition Impairment and Show Less Hepatotoxicity

  摘要：

  A series of tacrine-NO donor hybrid compounds are synthesized and evaluated for cholinesterase inhibitor), activity, cogonition improving activity, and hepatotoxicity. The pharmacological results indicate that hybrid compounds 1, 2, and 3a potently inhibit cholinesterase in vitro and significantly improve the scopolamine-induced cognition impairment, whereas an analogue (3h) of 2 without the NO donor moiety does not. Compared to tacrine, 1 and 2 show much less hepatotoxicity. Molecular modeling studies suggest that 2 may interact with the catalytic and the peripheral anionic site of acetylcholinesterase.

  DOI：

  10.1021/jm801131a

文献信息

• NO-Donating Tacrine Hybrid Compounds Improve Scopolamine-Induced Cognition Impairment and Show Less Hepatotoxicity
  作者：Lei Fang、Dorothea Appenroth、Michael Decker、Michael Kiehntopf、Amelie Lupp、Sixun Peng、Christian Fleck、Yihua Zhang、Jochen Lehmann

  DOI：10.1021/jm801131a

  日期：2008.12.25

  A series of tacrine-NO donor hybrid compounds are synthesized and evaluated for cholinesterase inhibitor), activity, cogonition improving activity, and hepatotoxicity. The pharmacological results indicate that hybrid compounds 1, 2, and 3a potently inhibit cholinesterase in vitro and significantly improve the scopolamine-induced cognition impairment, whereas an analogue (3h) of 2 without the NO donor moiety does not. Compared to tacrine, 1 and 2 show much less hepatotoxicity. Molecular modeling studies suggest that 2 may interact with the catalytic and the peripheral anionic site of acetylcholinesterase.