(3E,5E)-3,5-bis(4-(4-methylpiperazin-1-yl)benzylidene)piperidin-4-one | 1338000-42-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (3E,5E)-3,5-bis(4-(4-methylpiperazin-1-yl)benzylidene)piperidin-4-one
• 英文别名: (3E,5E)-3,5-bis[[4-(4-methylpiperazin-1-yl)phenyl]methylidene]piperidin-4-one
• CAS: 1338000-42-2
• 化学式: C₂₉H₃₇N₅O
• 分子量: 471.646
• InChiKey: PHJURBRZDOOZAJ-FQHZWJPGSA-N

物化性质

• 沸点：
  691.6±55.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3E,5E)-3,5-bis(4-(4-methylpiperazin-1-yl)benzylidene)piperidin-4-one 、 3-(bromomethyl)-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-oxyl 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以40%的产率得到(3E,5E)-1-((1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-yl)methyl)-3,5-bis(4-(4-methylpiperazin-1-yl)benzylidene)piperidin-4-one radical
  参考文献：
  名称：

  基于姜黄素-一氧化氮的抗氧化剂和抗增殖剂的合成及生物学评价。

  摘要：

  背景技术天然产物及其衍生物被广泛用于治疗与ROS和RNS诱导的损害有关的癌症和其他疾病。方法已设计，合成了一系列顺磁性修饰姜黄素类似物和3,5-二亚芳基哌啶酮（DAP），并具有抗增殖和抗氧化活性。结果新化合物的生物学特性支持了较早的结果，即在含有芳基羟基和/或甲氧基取代基的情况下，将氮氧化物部分或其前体掺入姜黄素或二芳基哌啶酮（DAP）支架中会导致对癌细胞系的抗增殖作用。衍生物，表明其潜在的靶向治疗应用。在碱性侧链衍生物的情况下，氮氧化物的引入产生了明确的结果，然而，趋向于更容易获得的DAP衍生物具有更强的抗增殖作用。在大多数情况下，氮氧化物的引入增加了DAP衍生物的TEAC值（质子和电子给体能力）。结论在合成和研究的化合物中，自旋标记的姜黄素和3,5-双（4-羟基-3-甲氧基亚苄基）哌啶-4-酮衍生物是最有效的抗增殖和抗氧化剂衍生物。

  DOI：

  10.2174/1871520617666170522124712
• 作为产物：
  描述：

  4-氧代哌啶酮盐酸盐 、 4-(4-甲基哌嗪)苯甲醛 在 盐酸 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 72.0h， 以67%的产率得到(3E,5E)-3,5-bis(4-(4-methylpiperazin-1-yl)benzylidene)piperidin-4-one
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of curcumin analogues as multifunctional agents for the treatment of Alzheimer’s disease

  摘要：

  A series of novel curcumin analogues were designed, synthesized, and evaluated as potential multifunctional agents for the treatment of AD. The in vitro studies showed that these compounds had better inhibitory properties against A beta aggregation than curcumin. Superior anti-oxidant properties (better than the reference compound Trolox) of these compounds were observed by the oxygen radical absorbance capacity (ORAC) method and a cell-based assay using DCFH-DA as a probe. In addition they were able to chelate metals such as iron and copper and decrease metal-induced A beta aggregation. The structure-activity relationships were discussed. The results suggested that our curcumin analogues could be selected as multifunctional agents for further investigation of AD treatment. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.033

文献信息

• Synthesis and Biological Evaluation of Curcumin-Nitroxide-Based Molecular Hybrids as Antioxidant and Anti-Proliferative Agents
  作者：Balazs Bognar、M. Lakshmi Kuppusamy、Esha Madan、Tamas Kalai、Maria Balog、Jozsef Jeko、Periannan Kuppusamy、Kalman Hideg

  DOI：10.2174/1871520617666170522124712

  日期：2017.11.8

  incorporation of a nitroxide moiety or its precursor into curcumin or diarylidenylpiperidone (DAP) scaffolds resulted in anti-proliferative effect toward cancerous cell-lines in case of aryl hydroxy and/or methoxy substituent containing derivatives, suggesting their potential for targeted therapeutic applications. In case of basic side chain derivatives, nitroxide incorporation gave unambiguous results, however

  背景技术天然产物及其衍生物被广泛用于治疗与ROS和RNS诱导的损害有关的癌症和其他疾病。方法已设计，合成了一系列顺磁性修饰姜黄素类似物和3,5-二亚芳基哌啶酮（DAP），并具有抗增殖和抗氧化活性。结果新化合物的生物学特性支持了较早的结果，即在含有芳基羟基和/或甲氧基取代基的情况下，将氮氧化物部分或其前体掺入姜黄素或二芳基哌啶酮（DAP）支架中会导致对癌细胞系的抗增殖作用。衍生物，表明其潜在的靶向治疗应用。在碱性侧链衍生物的情况下，氮氧化物的引入产生了明确的结果，然而，趋向于更容易获得的DAP衍生物具有更强的抗增殖作用。在大多数情况下，氮氧化物的引入增加了DAP衍生物的TEAC值（质子和电子给体能力）。结论在合成和研究的化合物中，自旋标记的姜黄素和3,5-双（4-羟基-3-甲氧基亚苄基）哌啶-4-酮衍生物是最有效的抗增殖和抗氧化剂衍生物。
• Design, synthesis, and biological evaluation of curcumin analogues as multifunctional agents for the treatment of Alzheimer’s disease
  作者：Shang-Ying Chen、Yuan Chen、Yan-Ping Li、Shu-Han Chen、Jia-Heng Tan、Tian-Miao Ou、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1016/j.bmc.2011.07.033

  日期：2011.9

  A series of novel curcumin analogues were designed, synthesized, and evaluated as potential multifunctional agents for the treatment of AD. The in vitro studies showed that these compounds had better inhibitory properties against A beta aggregation than curcumin. Superior anti-oxidant properties (better than the reference compound Trolox) of these compounds were observed by the oxygen radical absorbance capacity (ORAC) method and a cell-based assay using DCFH-DA as a probe. In addition they were able to chelate metals such as iron and copper and decrease metal-induced A beta aggregation. The structure-activity relationships were discussed. The results suggested that our curcumin analogues could be selected as multifunctional agents for further investigation of AD treatment. (C) 2011 Elsevier Ltd. All rights reserved.