(3E,5E)-3,5-bis(naphthalen-1-ylmethylidene)-1-prop-2-enoylpiperidin-4-one | 1312614-73-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3E,5E)-3,5-bis(naphthalen-1-ylmethylidene)-1-prop-2-enoylpiperidin-4-one
• CAS: 1312614-73-5
• 化学式: C₃₀H₂₃NO₂
• 分子量: 429.518
• InChiKey: MTRUEVQGINMHEH-RPCRKUJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3E,5E)-3,5-bis(naphthalen-1-ylmethylidene)-1-prop-2-enoylpiperidin-4-one 、 5-氯靛红 、 L-脯氨酸 以 甲醇 为溶剂， 反应 5.0h， 以75%的产率得到1"-carbonyl(spiro[2.3']-5-chlorooxindole-hexahydro-1H-pyrrolizine)-3",5"-bis[(E)-naphthylmethylidene]tetrahydro-4"(1H)-pyridinone
  参考文献：
  名称：

  螺旋吡咯并吲哚-吡咯烷嗪-哌啶杂种的化学，区域和立体选择性合成和胆碱酯酶抑制活性

  摘要：

  通过一系列1-丙烯酰基-3,5-双芳基亚甲基哌啶-4-的1,3-偶极环加成反应，以化学，区域和立体选择性高收率合成了一系列新的杂螺环杂环，包括吡咯嗪，螺氧并吲哚和哌啶部分具有在甲醇中由5-胆红素和1-脯氨酸原位产生的甲亚胺基亚胺的化合物。这些环加合物显示出显着的胆碱酯酶抑制活性。在筛选的化合物中，8g和8e表现出对乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）的最大抑制活性，IC 50值分别为3.33和3.13μM。

  DOI：

  10.1016/j.bmcl.2013.03.027
• 作为产物：
  描述：

  1-萘甲醛 在 盐酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 (3E,5E)-3,5-bis(naphthalen-1-ylmethylidene)-1-prop-2-enoylpiperidin-4-one
  参考文献：
  名称：

  螺旋吡咯并吲哚-吡咯烷嗪-哌啶杂种的化学，区域和立体选择性合成和胆碱酯酶抑制活性

  摘要：

  通过一系列1-丙烯酰基-3,5-双芳基亚甲基哌啶-4-的1,3-偶极环加成反应，以化学，区域和立体选择性高收率合成了一系列新的杂螺环杂环，包括吡咯嗪，螺氧并吲哚和哌啶部分具有在甲醇中由5-胆红素和1-脯氨酸原位产生的甲亚胺基亚胺的化合物。这些环加合物显示出显着的胆碱酯酶抑制活性。在筛选的化合物中，8g和8e表现出对乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）的最大抑制活性，IC 50值分别为3.33和3.13μM。

  DOI：

  10.1016/j.bmcl.2013.03.027

文献信息

• Synthesis and discovery of novel piperidone-grafted mono- and bis-spirooxindole-hexahydropyrrolizines as potent cholinesterase inhibitors
  作者：Yalda Kia、Hasnah Osman、Raju Suresh Kumar、Vikneswaran Murugaiyah、Alireza Basiri、Subbu Perumal、Habibah A. Wahab、Choi Sy Bing

  DOI：10.1016/j.bmc.2013.01.066

  日期：2013.4

  Three-component reaction of a series of 1-acryloyl-3,5-bisbenzylidenepiperidin-4-ones with isatin and L-proline in 1:1:1 and 1:2:2 molar ratios in methanol afforded, respectively the piperidone-grafted novel mono- and bisspiro heterocyclic hybrids comprising functionalized piperidine, pyrrolizine and oxindole ring systems in good yields. The in vitro evaluation of cholinesterase enzymes inhibitory activity of these cycloadducts disclosed that monospiripyrrolizines (8a-k), are more active with IC50 ranging from 3.36 to 20.07 mu M than either the dipolarophiles (5a-k) or bisspiropyrrolizines (9a-k). The compounds, 8i and 8e with IC50 values of 3.36 and 3.50 mu M, respectively showed the maximum inhibition of acethylcholinesterase (AChE) and butrylylcholinestrase (BuChE). Molecular modeling simulation, disclosed the binding interactions of the most active compounds to the active site residues of their respective enzymes. The docking results were in accordance with the IC50 values obtained from in vitro cholinesterase assay. (C) 2013 Elsevier Ltd. All rights reserved.
• A facile chemo-, regio- and stereoselective synthesis and cholinesterase inhibitory activity of spirooxindole–pyrrolizine–piperidine hybrids
  作者：Yalda Kia、Hasnah Osman、Raju Suresh Kumar、Vikneswaran Murugaiyah、Alireza Basiri、Subbu Perumal、Ibrahim Abdul Razak

  DOI：10.1016/j.bmcl.2013.03.027

  日期：2013.5

  A series of novel hybrid spiro heterocycles comprising pyrrolizine, spiroxindole and piperidine moieties was synthesized chemo-, regio- and stereoselectively in good yields from 1,3-dipolar cycloaddition reaction of a series of 1-acryloyl-3,5-bisarylmethylidenepiperidin-4-ones with azomethine ylides generated in situ from 5-choloroisatin and l-proline in methanol. These cycloadducts displayed significant

  通过一系列1-丙烯酰基-3,5-双芳基亚甲基哌啶-4-的1,3-偶极环加成反应，以化学，区域和立体选择性高收率合成了一系列新的杂螺环杂环，包括吡咯嗪，螺氧并吲哚和哌啶部分具有在甲醇中由5-胆红素和1-脯氨酸原位产生的甲亚胺基亚胺的化合物。这些环加合物显示出显着的胆碱酯酶抑制活性。在筛选的化合物中，8g和8e表现出对乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）的最大抑制活性，IC 50值分别为3.33和3.13μM。
• Ionic liquid mediated synthesis of mono- and bis-spirooxindole-hexahydropyrrolidines as cholinesterase inhibitors and their molecular docking studies
  作者：Yalda kia、Hasnah Osman、Raju Suresh Kumar、Alireza Basiri、Vikneswaran Murugaiyah

  DOI：10.1016/j.bmc.2014.01.002

  日期：2014.2

  One pot, three-component reaction of 1-acryloyl-3,5-bisarylmethylidenepiperidin-4-ones with isatin and sarcosine in molar ratios of 1: 1: 1 and 1: 2: 2 furnished to mono-and bis-spiropyrrolidine heterocyclic hybrids comprising functionalized piperidine, pyrrolidine and oxindole structural motifs. Both mono and bis-spiropyrrolidines displayed good inhibitory activity against acetylcholinesterase (AChE) with IC50 values of 2.36-9.43 mu M. For butyrylcholinesterase (BChE), mono-cycloadducts in series 8 with IC50 values of lower than 10 mu M displayed better inhibitory activities than their bis-cycloadduct analogs in series 9 with IC50 values of 7.44-19.12 mu M. The cycloadducts 9j and 8e were found to be the most potent AChE and BChE inhibitors with IC50 values of 2.35 and 3.21 mu M, respectively. Compound 9j was found to be competitive inhibitor of AChE while compound 8e was a mixed-mode inhibitor of BChE with calculated K-i values of 2.01 and 6.76 mu M, respectively. Molecular docking on Torpedo californica AChE and human BChE showed good correlation between IC50 values and free binding energy values of the synthesized compounds docked into the active site of the enzymes. (C) 2014 Elsevier Ltd. All rights reserved.