(E)-3-(4-hydroxy-3-methoxyphenyl)-N-[6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyl]acrylamide | 1374413-62-3

• 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: (E)-3-(4-hydroxy-3-methoxyphenyl)-N-[6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyl]acrylamide
• 英文别名: (E)-3-(4-hydroxy-3-methoxyphenyl)-N-[6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyl]prop-2-enamide
• CAS: 1374413-62-3
• 化学式: C₂₉H₃₅N₃O₃
• 分子量: 473.615
• InChiKey: KKKODFFFJFQMSI-BMRADRMJSA-N

物化性质

• 沸点：
  750.0±60.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.5
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,6-己二胺 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 戊醇 为溶剂， 反应 42.5h， 生成 (E)-3-(4-hydroxy-3-methoxyphenyl)-N-[6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyl]acrylamide
  参考文献：
  名称：

  Tacrine–Ferulic Acid–Nitric Oxide (NO) Donor Trihybrids as Potent, Multifunctional Acetyl- and Butyrylcholinesterase Inhibitors

  摘要：

  In search of multifunctional cholinesterase inhibitors as potential anti-Alzheimer drug candidates, tacrine-ferulic acid-NO donor trihybrids were synthesized and tested for their cholinesterase inhibitory activities, release of nitric oxide, vasodilator properties, cognition improving potency, and hepatotoxicity. All of the novel target compounds show higher in vitro cholinesterase inhibitory activity than tacrine. Three selected compounds (3a, 3f, and 3k) produce moderate vasorelaxation in vitro, which correlates with the release of nitric oxide. Compared to its non-nitrate dihybrid analogue (3u), the trihybrid 3f exhibits better performance in improving the scopolamine-induced cognition impairment (mice) and, furthermore, less hepatotoxicity than tacrine.

  DOI：

  10.1021/jm300106z

文献信息

• Tacrine–Ferulic Acid–Nitric Oxide (NO) Donor Trihybrids as Potent, Multifunctional Acetyl- and Butyrylcholinesterase Inhibitors
  作者：Yao Chen、Jianfei Sun、Lei Fang、Mei Liu、Sixun Peng、Hong Liao、Jochen Lehmann、Yihua Zhang

  DOI：10.1021/jm300106z

  日期：2012.5.10

  In search of multifunctional cholinesterase inhibitors as potential anti-Alzheimer drug candidates, tacrine-ferulic acid-NO donor trihybrids were synthesized and tested for their cholinesterase inhibitory activities, release of nitric oxide, vasodilator properties, cognition improving potency, and hepatotoxicity. All of the novel target compounds show higher in vitro cholinesterase inhibitory activity than tacrine. Three selected compounds (3a, 3f, and 3k) produce moderate vasorelaxation in vitro, which correlates with the release of nitric oxide. Compared to its non-nitrate dihybrid analogue (3u), the trihybrid 3f exhibits better performance in improving the scopolamine-induced cognition impairment (mice) and, furthermore, less hepatotoxicity than tacrine.