3,5-bis(naphthalen-1-ylmethylidene)piperidin-4-one | 1314761-72-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,5-bis(naphthalen-1-ylmethylidene)piperidin-4-one
• CAS: 1314761-72-2
• 化学式: C₂₇H₂₁NO
• 分子量: 375.47
• InChiKey: ZUOMENXXCRZTKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-氧代哌啶酮盐酸盐 、 1-萘甲醛 在 盐酸 、 potassium carbonate 作用下， 以 溶剂黄146 、 水 、 丙酮 为溶剂， 生成 3,5-bis(naphthalen-1-ylmethylidene)piperidin-4-one
  参考文献：
  名称：

  Microwave assisted synthesis, cholinesterase enzymes inhibitory activities and molecular docking studies of new pyridopyrimidine derivatives

  摘要：

  A series of hitherto unreported pyrido-pyrimidine-2-ones/pyrimidine-2-thiones were synthesized under microwave assisted solvent free reaction conditions in excellent yields and evaluated in vitro for their acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes inhibitory activity. Among the pyridopyrimidine derivatives, 7e and 7l displayed 2.5- and 1.5-fold higher enzyme inhibitory activities against AChE as compared to standard drug, galanthamine, with IC50 of 0.80 and 1.37 mu M, respectively. Interestingly, all the compounds except 6k, 7j and 7k displayed higher inhibitory potential against BChE enzyme in comparison to standard with IC50 ranging from 1.18 to 18.90 mu M. Molecular modeling simulations of 7e and 7l was performed using three-dimensional structure of Torpedo californica AChE (TcAChE) and human butyrylcholinesterase (hBChE) enzymes to disclose binding interaction and orientation of these molecule into the active site gorge of respective receptors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.058

文献信息

• Dipolar cycloaddition based multi-component reaction: Synthesis of spiro tethered acenaphthylene–indolizine–pyridinone hybrids
  作者：Raju Suresh Kumar、Abdulrahman I. Almansour、Natarajan Arumugam、Govindasami Periyasami、S. Athimoolam、Raju Ranjith Kumar、Mohammad Asad、Abdullah M. Asiri

  DOI：10.1016/j.tetlet.2018.07.051

  日期：2018.8

  novel dispiro acenaphthylene–indolizine–pyridinone hybrid heterocycles have been achieved through one-pot four-component domino 1,3-dipolar cycloaddition–Michael addition–air oxidation sequence of reactions.

  通过一锅四组分多米诺1，3-偶极环加成反应-迈克尔加成反应-空气氧化反应序列，实现了新型二螺o基-吲哚嗪-吡啶酮杂合杂环的立体选择性合成。