(E)-3-{3-methoxy-4-[2-(nitrooxy)ethoxy]phenyl} acrylic acid | 1374413-63-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-{3-methoxy-4-[2-(nitrooxy)ethoxy]phenyl} acrylic acid
• 英文别名: (E)-3-[3-methoxy-4-(2-nitrooxyethoxy)phenyl]prop-2-enoic acid
• CAS: 1374413-63-4
• 化学式: C₁₂H₁₃NO₇
• 分子量: 283.238
• InChiKey: WXYQLRQBMASZKE-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-3-{3-methoxy-4-[2-(nitrooxy)ethoxy]phenyl} acrylic acid 、 N-(1,2,3,4-tetrahydroacridin-9-yl)octane-1,8-diamine 在 N,N'-二环己基碳二亚胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 以31%的产率得到2-{2-methoxy-4-[(1E)-3-oxo-3-(8-(1,2,3,4-tetrahydroacridin-9-ylamino)octylamino)prop-1-enyl]phenoxy}ethyl nitrate
  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
• 作为产物：
  描述：

  methyl (E)-3-(4-(2-bromoethoxy)-3-methoxyphenyl)acrylate 在 水 、 silver nitrate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 30.0h， 生成 (E)-3-{3-methoxy-4-[2-(nitrooxy)ethoxy]phenyl} acrylic acid
  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

• 一种法舒地尔衍生物及其制备方法和应用
  申请人：沈阳药科大学

  公开号：CN116375685A

  公开（公告）日：2023-07-04

  本发明提供了一种法舒地尔衍生物及其制备方法和应用，属于医药合成技术领域。本发明提供的法舒地尔衍生物，具有式I所示结构；法舒地尔是ROCK抑制剂，通过抑制ROCK起到强效扩张血管、保护神经元细胞、促进轴突再生、保护缺血脑组织的作用。本发明以法舒地尔作为母核结构，制得的法舒地尔衍生物自由基清除效率高，副作用小，抑制炎症因子效力强，抗氧化应激能力好，能够用于制备神经保护及治疗脑卒中疾病的药物。
• 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.