(3E,5E)-3,5-bis(4-hydroxybenzylidene)piperidin-4-one hydrochloride

• 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(4-hydroxybenzylidene)piperidin-4-one hydrochloride
• 英文别名: (3E,5E)-3,5-bis(4-hydroxybenzylidene)-4-piperidone hydrochloride；3,5-bis(4-hydroxybenz-(E)-ylidene)-4-piperidone hydrochloride；(3E,5E)-3,5-bis[(4-hydroxyphenyl)methylidene]piperidin-4-one;hydrochloride
• 化学式: C₁₉H₁₇NO₃*ClH
• 分子量: 343.81
• InChiKey: LEBARPOPRBOOME-XETSTSIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  69.6
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3E,5E)-3,5-bis(4-hydroxybenzylidene)piperidin-4-one hydrochloride 在 1-丙基磷酸酐 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-{3-[4-(3-aminopropylamino)butylamino]propyl}-4-[3,5-bis-(4-hydroxybenzylidene)-4-oxopiperidin-1-yl]-4-oxo-butanamide tri(trifluoroacetate)
  参考文献：
  名称：

  多胺共轭作为在阿尔茨海默氏病框架内靶向淀粉样蛋白聚集的有前途的策略

  摘要：

  精胺缀合物2 - 6，携带各种装饰3,5- dibenzylidenepiperidin -4-酮作为生物活性动机，被设计成引导antiaggregating属性到线粒体，使用多胺的功能的车辆的工具。研究证实线粒体邻苯二酚衍生物2的进口对Aβ诱导的毒性具有有效的抗聚集活性和神经保护作用。值得注意的是，还没有阐明聚胺基序在Aβ分子识别中的关键功能。在计算机模拟研究的支持下，该实验读数为聚胺的作用提供了重要的新见解。因此，我们提出多胺缀合作为开发神经保护剂导线的有前途的策略，可能有助于破译Aβ毒性的复杂图景。

  DOI：

  10.1021/acsmedchemlett.6b00339
• 作为产物：
  描述：

  4-氧代哌啶酮盐酸盐 、 对羟基苯甲醛 在 盐酸 、 溶剂黄146 作用下， 反应 48.0h， 以68%的产率得到(3E,5E)-3,5-bis(4-hydroxybenzylidene)piperidin-4-one hydrochloride
  参考文献：
  名称：

  多胺共轭作为在阿尔茨海默氏病框架内靶向淀粉样蛋白聚集的有前途的策略

  摘要：

  精胺缀合物2 - 6，携带各种装饰3,5- dibenzylidenepiperidin -4-酮作为生物活性动机，被设计成引导antiaggregating属性到线粒体，使用多胺的功能的车辆的工具。研究证实线粒体邻苯二酚衍生物2的进口对Aβ诱导的毒性具有有效的抗聚集活性和神经保护作用。值得注意的是，还没有阐明聚胺基序在Aβ分子识别中的关键功能。在计算机模拟研究的支持下，该实验读数为聚胺的作用提供了重要的新见解。因此，我们提出多胺缀合作为开发神经保护剂导线的有前途的策略，可能有助于破译Aβ毒性的复杂图景。

  DOI：

  10.1021/acsmedchemlett.6b00339

文献信息

• Curcumin Analogs as Potent Aldose Reductase Inhibitors
  作者：Zhi-Yun Du、Ya-Dan Bao、Zhong Liu、Wei Qiao、Lin Ma、Zhi-Shu Huang、Lian-Quan Gu、Albert S. C. Chan

  DOI：10.1002/ardp.200500205

  日期：2006.3

  study, curcuminoids isolated from curcuma longa were demonstrated to possess inhibitory activities on bovine lens aldose reductase. In order to find more potent aldose reductase inhibitor, curcumin analogs were synthesized and evaluated for their ability to inhibit bovine lens aldose reductase enzyme. The results indicated that the compounds with tetrahydroxyl groups, 2,6‐bis(3,4‐dihydroxybenzylidene)cyclohexanone

  在本研究中，从姜黄中分离的姜黄素被证明对牛晶状体醛糖还原酶具有抑制活性。为了找到更有效的醛糖还原酶抑制剂，合成了姜黄素类似物并评估了它们抑制牛晶状体醛糖还原酶的能力。结果表明，具有四羟基基团的化合物、2,6-双(3,4-二羟基亚苄基)环己酮(A2)、2,5-双(3,4-二羟基亚苄基)环戊酮(B2)、1,5-双( 3,4-二羟基苯基)-1,4-戊二烯-3-一(C2)和3,5-双(3,4-二羟基苯亚甲基)-4-哌啶酮(D2)对醛糖还原酶具有显着的抑制作用，IC50分别为 2.9 μM、2.6 μM、3.4 μM 和 4.9 μM。
• α-Glucosidase inhibition of natural curcuminoids and curcumin analogs
  作者：Zhi-yun Du、Rong-rong Liu、Wei-yan Shao、Xue-pu Mao、Lin Ma、Lian-quan Gu、Zhi-shu Huang、Albert S.C. Chan

  DOI：10.1016/j.ejmech.2005.10.012

  日期：2006.2

  Natural curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3) isolated from Curcuma longa (turmeric), and synthetic curcumin analogs (A(1-7), B1-7, C1-6 and D1-7) were evaluated in vitro for the a-glucosidase inhibitory activity via UV and circular dichroism (CD) spectroscopy. The results indicated that natural curcuminoid compound 3 showed a remarkable inhibitory effect with IC50 of 23.0 mu M, and the synthetic compounds A(2), B-2, C-2 and D-2 showed potent inhibitory effects with IC50 of 2.8, 2.6, 1.6 and 8.2 mu M, respectively. Kinetic study exhibited that the mechanism of alpha-glucosidase inhibition of both 3 and C-2 was non-competitive. The structure activity relationship revealed that the ortho dihydroxyl groups could form a more tight interaction with a-glucosidase to exert more potential inhibitory activities. (c) 2006 Elsevier SAS. All fights reserved.
• Synthesis and evaluation of curcumin-related compounds for anticancer activity
  作者：Xingchuan Wei、Zhi-Yun Du、Xi Zheng、Xiao-Xing Cui、Allan H. Conney、Kun Zhang

  DOI：10.1016/j.ejmech.2012.04.005

  日期：2012.7

  Sixty-one curcumin-related compounds were synthesized and evaluated for their anticancer activity toward cultured prostate cancer PC-3 cells, pancreas cancer Panc-1 cells and colon cancer HT-29 cells. Inhibitory effects of these compounds on the growth of PC-3. Panc-1 and HT-29 cells were determined by the MTT assay. Compounds E10, F10, FN1 and FN2 exhibited exceptionally potent inhibitory effects on the growth of cultured PC-3, Panc-1 and HT-29 cells. The IC50 for these compounds was lower than 1 mu M in all three cell lines. E10 was 72-, 46- and 117-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. F10 was 69-, 34- and 72-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. FN1 and FN2 had about the same inhibitory effect as E10 and F10 toward Panc-1 cells but were less active than E10 and F10 toward PC-3 and HT-29 cells. The active compounds were potent stimulators of apoptosis. The present study indicates that E10, F10, FN1 and FN2 may have useful anticancer activity. (C) 2012 Elsevier Masson SAS. All rights reserved.