(3E,5E)-1-benzyl-3,5-bis(3,4-dihydroxybenzylidene)piperidin-4-one

• 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)-1-benzyl-3,5-bis(3,4-dihydroxybenzylidene)piperidin-4-one
• 英文别名: 1-Benzyl-3,5-bis(3,4-dihydroxybenzylidene)piperidin-4-one；(3E,5E)-1-benzyl-3,5-bis[(3,4-dihydroxyphenyl)methylidene]piperidin-4-one
• 化学式: C₂₆H₂₃NO₅
• 分子量: 429.472
• InChiKey: MRNIEEPMKYWDTA-CLVAPQHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  101
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-苄基哌啶酮 、 3,4-二羟基苯甲醛 在 盐酸 作用下， 以 乙醇 为溶剂， 以50.8%的产率得到(3E,5E)-1-benzyl-3,5-bis(3,4-dihydroxybenzylidene)piperidin-4-one
  参考文献：
  名称：

  设计，合成和评估NDGA类似物作为潜在的抗缺血性卒中药物

  摘要：

  外源补充具有清除ROS活性的抗氧化剂可能是中风脑缺血再灌注损伤的一种潜在疗法。在本研究中，设计和合成了一系列通过直接清除ROS以及通过keap1 / Nrf2 / ARE途径间接激活而具有降低氧化应激作用的NDGA类似物。发现所有类似物均可通过DPPH自由基清除法直接有效去除ROS，化合物3a通过促进Nrf2易位进入细胞核并增加血红素加氧酶-1（HO-1）的表达，有效保护PC12细胞免受氧化损伤。间接强烈降低细胞内ROS水平。更重要的是3a显着减少了短暂性脑中动脉闭塞（MCAO）大鼠的脑缺血再灌注损伤后的脑梗塞。总体而言，我们的发现表明化合物3a可以作为治疗中风的有前途的化合物。

  DOI：

  10.1016/j.ejmech.2017.09.028

文献信息

• 2,6-Bis(3,4,5-trihydroxybenzylydene) derivatives of cyclohexanone
  作者：Roberta Costi、Roberto Di Santo、Marino Artico、Silvio Massa、Rino Ragno、Roberta Loddo、Massimiliano La Colla、Enzo Tramontano、Paolo La Colla、Alessandra Pani

  DOI：10.1016/j.bmc.2003.10.005

  日期：2004.1

  A number of 2,6-bisbenzylidenecyclohexane-1-one derivatives have been synthesized and tested as HIV-1 integrase (IN) inhibitors with the aim of obtaining compounds capable to elicit antiviral activity at non-cytotoxic concentrations in cell-based assays. 3,5-Bis(3,4,5-trihydroxybenzylidene)-4-oxocyclohexaneacetic acid (20d) resulted one of the most potent and selective derivatives in acutely infected MT-4 cells (EC50 and CC50 values of 2 and 40 muM, respectively). In enzyme assays with recombinant HIV-1 integrase (rIN), this compound proved able to inhibit both 3'-processing and disintegration with IC50 values of 0.2 and 0.5 muM, respectively. In order to develop a model capable to predict the anti HIV-IN activity and useful to design novel derivatives, we performed a comparative molecular field analysis (CoMFA) like 3-D-QSAR. In our model the ligands were described quantitatively in the GRID program, and the model was optimized by selecting only the most informative variables in the GOLPE program. We found the predictive ability of the model to increase significantly when the number of variables was reduced from 20,925 to 1327. A Q(2) of 0.73 was obtained with the final model, confirming the predictive ability of the model. By studying the PLS coefficients in informative 3-D contour plots, ideas for the synthesis of new compounds could be generated. (C) 2003 Elsevier Ltd. All rights reserved.