(3E,5E)-3,5-bis(2-fluorobenzyl)piperidin-4-one | 1246964-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3E,5E)-3,5-bis(2-fluorobenzyl)piperidin-4-one
• 英文别名: 3,5-bis(2-fluorobenzyl)-4-piperidone；3,5-bis[(2-fluorophenyl)methyl]piperidin-4-one
• CAS: 1246964-13-5
• 化学式: C₁₉H₁₉F₂NO
• 分子量: 315.363
• InChiKey: VDLGLERMFJOPQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  EF24 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 以95%的产率得到(3E,5E)-3,5-bis(2-fluorobenzyl)piperidin-4-one
  参考文献：
  名称：

  CLEFMA—An anti-proliferative curcuminoid from structure–activity relationship studies on 3,5-bis(benzylidene)-4-piperidones

  摘要：

  3,5-Bis(benzylidene)-4-piperidones are being advanced as synthetic analogs of curcumin for anti-cancer and anti-inflammatory properties. We performed structure-activity relationship studies, by testing several synthesized 3,5-bis(benzylidene)-4-piperidones for anti-proliferative activity in lung adenocarcinoma H441 cells. Compared to the lead compound 1, or 3,5-bis(2-fluorobenzylidene)-4-piperidone, five compounds were found to be more potent (IC50 <30 mu M), and 16 compounds possessed reduced cell-killing efficacy (IC50 >50 mu M). Based on the observations, we synthesized 4-[3,5-bis(2-chlorobenzyl-idene-4-oxo-piperidine-1-yl)-4-oxo-2-butenoic acid] (29 or CLEFMA) as a novel analog of 1. CLEFMA was evaluated for anti-proliferative activity in H441 cells, and was found to be several folds more potent than compound 1. We did not find apoptotic cell population in flow cytometry, and the absence of apoptosis was confirmed by the lack of caspase cleavage. The electron microscopy of H441cells indicated that CLEFMA and compound 1 induce autophagic cell death that was inhibited by specific autophagy inhibitor 3-methyladenine. The results suggest that the potent and novel curcuminoid, CLEFMA, offers an alternative mode of cell death in apoptosis-resistant cancers. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.055

文献信息

• ANTIPROLIFERATIVE COMPOSITIONS COMPRISING CURCUMIN ANALOGS AND METHODS OF PRODUCING AND USING SAME
  申请人：Awasthi Vibhudutta

  公开号：US20120288555A1

  公开（公告）日：2012-11-15

  Antiproliferative compositions that include CLEFMA, as well as liposomal compositions containing said antiproliferative compositions, are disclosed. Also disclosed are methods of making and using the antiproliferative compositions and liposomal compositions.

  本文披露了包含CLEFMA的抗增殖组合物，以及含有该抗增殖组合物的脂质体组合物。还披露了制备和使用抗增殖组合物和脂质体组合物的方法。
• Antiproliferative compositions comprising curcumin analogs and methods of producing and using same
  申请人：Awasthi Vibhudutta

  公开号：US09359196B2

  公开（公告）日：2016-06-07

  Antiproliferative compositions that include CLEFMA, as well as liposomal compositions containing said antiproliferative compositions, are disclosed. Also disclosed are methods of making and using the antiproliferative compositions and liposomal compositions.

  本发明揭示了包括CLEFMA的抗增殖组合物，以及含有所述抗增殖组合物的脂质体组合物。还揭示了制备和使用抗增殖组合物和脂质体组合物的方法。
• Developing dietary curcumin mono-carbonyl piperidinone analogs as Nrf2-dependent cytoprotectors against oxidative damage: Structure-activity relationship and mechanisms
  作者：Xue-Feng Liu、Qi Wang、Jia-Fang Zheng、Zuo-Hu Chai、Fang Dai、Xiao-Jie Jin、Bo Zhou

  DOI：10.1016/j.freeradbiomed.2022.05.009

  日期：2022.6
• US9359196B2
  申请人：——

  公开号：US9359196B2

  公开（公告）日：2016-06-07