1-cinnamoylpiperidin-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-cinnamoylpiperidin-2-one
• 英文别名: N-Cinnamoylpiperidin-2-one；1-[(E)-3-phenylprop-2-enoyl]piperidin-2-one
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: ZRSPPDNPJCRTRU-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  乙醇 、 1-cinnamoylpiperidin-2-one 在 三乙胺 作用下， 反应 8.0h， 以70%的产率得到反式-肉桂酸乙酯
  参考文献：
  名称：

  N-酰基-2-哌啶酮的轻度，无金属和无保护的氨基转移为氨基酸，氨基醇和脂肪胺以及N-酰基-2-哌啶酮的酯化

  摘要：

  一种高选择性，温和且无金属的方案，可在短反应时间（30–45分钟）内将N-酰基哌啶酮转氨成未保护的氨基酸，氨基醇和其他脂肪族胺，且无其他碱且在纯净条件下进行。N酰基哌啶酮在85°C下用脂肪族醇酯化。酰胺键捻，τ= -20.39°和pyramidalization，χ Ñ = -11.73°。

  DOI：

  10.1002/ejoc.201900517
• 作为产物：
  描述：

  肉桂酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 1-cinnamoylpiperidin-2-one
  参考文献：
  名称：

  Meta-substituted piperlongumine derivatives attenuate inflammation in both RAW264.7 macrophages and a mouse model of colitis

  摘要：

  DOI：

  10.1016/j.bioorg.2021.105465

文献信息

• Synthesis, Characterization, and Molecular Docking Studies of N-Acylated Butyro and Valerolactam Derivatives with Antiproliferative and Cytotoxic Activities
  作者：Mark Tristan J. Quimque、Mark John P. Mandigma、Justin Allen K. Lim、Simon Budde、Hans-Martin Dahse、Oliver B. Villaflores、Arnold V. Hallare、Allan Patrick G. Macabeo

  DOI：10.2174/1570180816666190716141524

  日期：2020.6.29

  cinnamoyl (8) butyrolactams, and, the crotonylated (10), trifluoromethylated (13), and chlorinated (14) cinnamoyl valerolactam derivatives as the most antiproliferative against human myeloid leukemia cells. The trifluoromethylated cinnamoyl valerolactam (13) displayed the best selectivity on K-562 cells. Molecular docking studies of 13 against tyrosine kinase provided evidence as tyrosine kinase inhibitor

  背景：带有迈克尔受体的亲电子化合物在抗癌药物发现中具有广阔的前景。 方法：从具有细胞毒性的Piper内酰胺生物碱中提取灵感，制备了12种N-酰化的丁酰和戊内酰胺，并评估了它们对正常人脐静脉内皮细胞（HUVEC），慢性人髓样白血病细胞（K-562）的抗增殖和细胞毒性活性，和Henrietta Lacks（HeLa）细胞用作模型细胞系。针对酪氨酸激酶进行生物活性衍生物的分子对接。 结果：MTT分析的结果表明，巴豆酰化（5）和含硝基的肉桂酰（8）丁内酰胺，以及巴豆酰化（10），三氟甲基化（13）和氯化（14）的肉桂酰戊内酰胺衍生物对人的抗增殖性最强髓样白血病细胞。三氟甲基化肉桂酰基戊内酰胺（13）在K-562细胞上显示出最佳选择性。13对酪氨酸激酶的分子对接研究提供了酪氨酸激酶抑制剂的证据，具有与伊马替尼相当的结合能和受体相互作用。 结论：亲电性N-丙烯酸部分的存在有助于该化合物作为开发抗白血病药物的灵感的潜力。
• The potential role of the 5,6-dihydropyridin-2(1<i>H</i>)-one unit of piperlongumine on the anticancer activity
  作者：Wen-Wen Mu、Peng-Xiao Li、Yue Liu、Jie Yang、Guo-Yun Liu

  DOI：10.1039/d0ra08778e

  日期：——

  Piperlongumine (PL), a potent anticancer agent from the plant long pepper (Piper longum), contains the 5,6-dihydropyridin-2(1H)-one heterocyclic scaffold and cinnamoyl unit. In this paper, we synthesized a series of PL analogs and evaluated their cytotoxicity against cancer cells for the sake of exploring which pharmacophore plays a more potent role in enhancing the anticancer activities of PL. These results

  Piperlongumine ( PL ) 是一种来自植物长辣椒 ( Piper longum )的强效抗癌剂，含有 5,6-dihydropyridin-2(1 H )-one 杂环支架和肉桂酰基单元。在本文中，我们合成了一系列PL类似物并评估了它们对癌细胞的细胞毒性，以探索哪种药效团在增强PL的抗癌活性方面发挥更有效的作用。这些结果说明取代基的位置效应而非电子效应在PL及其类似物的细胞毒性中起一定作用。更重要的是，5,6-dihydropyridin-2(1 H)-一个单元，一种增强PL抗增殖活性的有效药效团，可与半胱胺反应并导致 ROS 产生，进而引起 ROS 诱导的下游事件的发生，进而导致细胞周期停滞和细胞凋亡。这项工作表明，引入含有迈克尔受体的内酰胺单元可能是增强药物抗癌活性的有效策略。
• Synthesis of Piperlongumine Analogues and Discovery of Nuclear Factor Erythroid 2-Related Factor 2 (Nrf2) Activators as Potential Neuroprotective Agents
  作者：Shoujiao Peng、Baoxin Zhang、Xianke Meng、Juan Yao、Jianguo Fang

  DOI：10.1021/acs.jmedchem.5b00410

  日期：2015.7.9

  The cellular antioxidant system plays key roles in blocking or retarding the pathogenesis of adult neurodegenerative disorders as elevated oxidative stress has been implicated in the pathophysiology of such diseases. Molecules with the ability in enhancing the antioxidant defense thus are promising candidates as neuroprotective agents. We reported herein the synthesis of piperlongumine analogues and evaluation of their cytoprotection against hydrogen peroxide- and 6-hydroxydopamine-induced neuronal cell oxidative damage in the neuron-like PC12 cells. The structure-activity relationship was delineated after the cytotoxicity and protection screening. Two compounds (4 and 5) displayed low cytotoxicity and confer potent protection of PC12 cells from the oxidative injury via upregulation of a panel of cellular antioxidant molecules. Genetically silencing the transcription factor Nrf2, a master regulator of the cellular stress responses, suppresses the cytoprotection, indicating the critical involvement of Nrf2 for the cellular action of compounds 4 and 5 in PC12 cells.
• Can an aromatic ring alter the reactions of a nearby unsaturated imide? A study of the rate and selectivity of nitrile oxide cycloaddition reactions of acryloyl derivatives of the Rebek imide benzoxazole
  作者：Dennis P. Curran、Moon-Hwan Yoon

  DOI：10.1016/s0040-4020(96)01167-2

  日期：1997.2

  Cycloadditions of acryloyl derivatives of the Rebek imide benzoxazole are extraordinarily stereoselective, but have rates and regioselectivities that otherwise parallel those of a simple achiral model. It appears that the benzoxazole ring of these compounds completely shields the inner face of the nearby alkene, but has no measurable effect on the rate of reactions on the outer face. (C) 1997, Elsevier Science Ltd.
• US4499100A
  申请人：——

  公开号：US4499100A

  公开（公告）日：1985-02-12