spiro-[2.3']-oxindole-spiro[3.3"]-1"-carbonyl(spiro[2.3']oxindole-5-phenyl pyrrolo)-5"-(naphthalen-1-methylidene)tetrahydro-4"-(1H)-pyridinone-4-(1-naphthyl)-5-phenylpyrrolidine

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: spiro-[2.3']-oxindole-spiro[3.3"]-1"-carbonyl(spiro[2.3']oxindole-5-phenyl pyrrolo)-5"-(naphthalen-1-methylidene)tetrahydro-4"-(1H)-pyridinone-4-(1-naphthyl)-5-phenylpyrrolidine
• 化学式: C₆₀H₄₇N₅O₄
• 分子量: 902.064
• InChiKey: JYQQDFZGMIWZQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.95
• 重原子数：
  69.0
• 可旋转键数：
  5.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  119.64
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  3,5-bis(naphthalen-1-ylmethylidene)piperidin-4-one 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 spiro-[2.3']-oxindole-spiro[3.3"]-1"-carbonyl(spiro[2.3']oxindole-5-phenyl pyrrolo)-5"-(naphthalen-1-methylidene)tetrahydro-4"-(1H)-pyridinone-4-(1-naphthyl)-5-phenylpyrrolidine
  参考文献：
  名称：

  Synthesis and discovery of highly functionalized mono- and bis-spiro-pyrrolidines as potent cholinesterase enzyme inhibitors

  摘要：

  Novel mono and bis spiropyrrolidine derivatives were synthesized via an efficient ionic liquid mediated, 1,3-dipolar cycloaddition methodology and evaluated in vitro for their AChE and BChE inhibitory activities in search for potent cholinesterase enzyme inhibitors. Most of the synthesized compounds displayed remarkable AChE inhibitory activities with IC50 values ranging from 1.68 to 21.85 mu M, wherein compounds 8d and 8j were found to be most active inhibitors against AChE and BChE with IC50 values of 1.68 and 2.75 mu M, respectively. Molecular modeling simulation on Torpedo californica AChE and human BChE receptors, showed good correlation between IC50 values and binding interaction template of the most active inhibitors docked into the active site of their relevant enzymes. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.019

文献信息

• Synthesis and discovery of highly functionalized mono- and bis-spiro-pyrrolidines as potent cholinesterase enzyme inhibitors
  作者：Yalda Kia、Hasnah Osman、Raju Suresh Kumar、Alireza Basiri、Vikneswaran Murugaiyah

  DOI：10.1016/j.bmcl.2014.02.019

  日期：2014.4

  Novel mono and bis spiropyrrolidine derivatives were synthesized via an efficient ionic liquid mediated, 1,3-dipolar cycloaddition methodology and evaluated in vitro for their AChE and BChE inhibitory activities in search for potent cholinesterase enzyme inhibitors. Most of the synthesized compounds displayed remarkable AChE inhibitory activities with IC50 values ranging from 1.68 to 21.85 mu M, wherein compounds 8d and 8j were found to be most active inhibitors against AChE and BChE with IC50 values of 1.68 and 2.75 mu M, respectively. Molecular modeling simulation on Torpedo californica AChE and human BChE receptors, showed good correlation between IC50 values and binding interaction template of the most active inhibitors docked into the active site of their relevant enzymes. (c) 2014 Elsevier Ltd. All rights reserved.