(S)-3,4-dimethoxy-N-[3-(2-oxo-1,2,5,6,7,8-hexahydroquinolin-5-ylamino)-propyl]benzamide | 1421022-02-7

• 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: (S)-3,4-dimethoxy-N-[3-(2-oxo-1,2,5,6,7,8-hexahydroquinolin-5-ylamino)-propyl]benzamide
• 英文别名: 3,4-dimethoxy-N-[3-[[(5S)-2-oxo-5,6,7,8-tetrahydro-1H-quinolin-5-yl]amino]propyl]benzamide
• CAS: 1421022-02-7
• 化学式: C₂₁H₂₇N₃O₄
• 分子量: 385.463
• InChiKey: HTYZDUJHLYRIMI-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  88.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基苯甲酰氯 在 氯化亚砜 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 14.0h， 生成 (S)-3,4-dimethoxy-N-[3-(2-oxo-1,2,5,6,7,8-hexahydroquinolin-5-ylamino)-propyl]benzamide
  参考文献：
  名称：

  Design, synthesis and evaluation of novel heterodimers of donepezil and huperzine fragments as acetylcholinesterase inhibitors

  摘要：

  Four series of novel heterodimers comprised of donepezil and huperzine A (HupA) fragments were designed, synthesized, and evaluated in search of potent acetylcholinesterase (AChE) inhibitors as potential therapeutic treatment for Alzheimer's disease. Heterodimers comprised of dimethoxyindanone (from donepezil), hupyridone (from HupA), and connected with a multimethylene linker, were identified as potent and selective inhibitors of AChE. Diastereomeric heterodimers (RS,S)-17b (with a tetramethylene linker) exhibited the highest potency of inhibition towards AChE with an IC50 value of 9 nM and no detectable inhibitory effect on butyrylcholinesterase at 1 mM. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.044

文献信息

• Design, synthesis and evaluation of novel heterodimers of donepezil and huperzine fragments as acetylcholinesterase inhibitors
  作者：Yueqing Hu、Jun Zhang、Oormila Chandrashankra、Fanny C.F. Ip、Nancy Y. Ip

  DOI：10.1016/j.bmc.2012.11.044

  日期：2013.2

  Four series of novel heterodimers comprised of donepezil and huperzine A (HupA) fragments were designed, synthesized, and evaluated in search of potent acetylcholinesterase (AChE) inhibitors as potential therapeutic treatment for Alzheimer's disease. Heterodimers comprised of dimethoxyindanone (from donepezil), hupyridone (from HupA), and connected with a multimethylene linker, were identified as potent and selective inhibitors of AChE. Diastereomeric heterodimers (RS,S)-17b (with a tetramethylene linker) exhibited the highest potency of inhibition towards AChE with an IC50 value of 9 nM and no detectable inhibitory effect on butyrylcholinesterase at 1 mM. (C) 2012 Elsevier Ltd. All rights reserved.