(S)-N-[5-(2-benzyloxy-5,6,7,8-tetrahydroquinolin-5-ylamino)-pentyl]-3,4-dimethoxybenzamide | 1421022-01-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-[5-(2-benzyloxy-5,6,7,8-tetrahydroquinolin-5-ylamino)-pentyl]-3,4-dimethoxybenzamide
• CAS: 1421022-01-6
• 化学式: C₃₀H₃₇N₃O₄
• 分子量: 503.641
• InChiKey: ZMRPOJACZKOSLE-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  37.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  81.71
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-N-[5-(2-benzyloxy-5,6,7,8-tetrahydroquinolin-5-ylamino)-pentyl]-3,4-dimethoxybenzamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以51%的产率得到(S)-3,4-dimethoxy-N-[5-(2-oxo-1,2,5,6,7,8-hexahydro-quinolin-5-ylamino)pentyl]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
• 作为产物：
  描述：

  3,4-二甲氧基苯甲酰氯 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 10.0h， 生成 (S)-N-[5-(2-benzyloxy-5,6,7,8-tetrahydroquinolin-5-ylamino)-pentyl]-3,4-dimethoxybenzamide
  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