2-{2'-fluoro-4'-[1-oxo-1-(8-(1,2,3,4-tetrahydroacridin-9-ylamino)octylamino)propan-2-yl]biphenyl-4-yloxy}ethyl nitrate | 1430219-42-3

• 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: 2-{2'-fluoro-4'-[1-oxo-1-(8-(1,2,3,4-tetrahydroacridin-9-ylamino)octylamino)propan-2-yl]biphenyl-4-yloxy}ethyl nitrate
• 英文别名: 2-[4-[2-Fluoro-4-[1-oxo-1-[8-(1,2,3,4-tetrahydroacridin-9-ylamino)octylamino]propan-2-yl]phenyl]phenoxy]ethyl nitrate；2-[4-[2-fluoro-4-[1-oxo-1-[8-(1,2,3,4-tetrahydroacridin-9-ylamino)octylamino]propan-2-yl]phenyl]phenoxy]ethyl nitrate
• CAS: 1430219-42-3
• 化学式: C₃₈H₄₅FN₄O₅
• 分子量: 656.798
• InChiKey: NEQBDGIZCFQZDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  氟比洛芬 在 aluminum (III) chloride 、 lithium hydroxide monohydrate 、 硫酸 、 potassium carbonate 、 silver nitrate 、 间氯过氧苯甲酸 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 116.5h， 生成 2-{2'-fluoro-4'-[1-oxo-1-(8-(1,2,3,4-tetrahydroacridin-9-ylamino)octylamino)propan-2-yl]biphenyl-4-yloxy}ethyl nitrate
  参考文献：
  名称：

  Design, synthesis and evaluation of tacrine–flurbiprofen–nitrate trihybrids as novel anti-Alzheimer’s disease agents

  摘要：

  To search for multifunctional anti-Alzheimer's disease (AD) agents with good safety, the previously synthesized tacrine-flurbiprofen hybrids 1a and 1b were modified into tacrine-flurbiprofen-nitrate trihybrids 3a-h. These compounds displayed comparable or higher cholinesterase inhibitory activity relative to the bivalent hybrids. Compound 3a was the most potent, which released moderate NO, exerted blood vessel relaxative activity, and showed significant A beta inhibitory effects whereas tacrine and flurbiprofen did not exhibit any Ab inhibitory activity at the same dose. In addition, 3a was active in improving memory impairment in vivo. More importantly, the hepatotoxicity study showed that 3a was much safer than tacrine, suggesting it might be a promising anti-AD agent for further investigation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.005