(1E,6E)-1,7-bis(4-hydroxy-3,5-dimethoxyphenyl)hepta-1,6-diene-3,5-dione | 189181-32-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (1E,6E)-1,7-bis(4-hydroxy-3,5-dimethoxyphenyl)hepta-1,6-diene-3,5-dione
• 英文别名: 1,7-bis(4-hydroxy-3,5-dimethoxyphenyl)-1,6-heptadiene-3,5-dione
• CAS: 189181-32-6
• 化学式: C₂₃H₂₄O₈
• 分子量: 428.439
• InChiKey: POWBSRUMKJEPOH-KQQUZDAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  顺-双(2,2'-二吡啶基)二氯化钌(II)二水合物 、 (1E,6E)-1,7-bis(4-hydroxy-3,5-dimethoxyphenyl)hepta-1,6-diene-3,5-dione 在 sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以44%的产率得到
  参考文献：
  名称：

  含有姜黄素配体的抗增殖钌复合物在人卵巢肿瘤细胞系 A2780 上进行了体外测试，发现它们调节 NF-κB 转录因子、FGF-2 生长因子和 MMP-9 通路的能力

  摘要：

  到目前为止，姜黄的多酚成分已显示出对包括肿瘤疾病在内的多种疾病的显着药理预防活性。这种类型的天然产物可能对抑制癌细胞增殖非常感兴趣，与经典化疗药物相比，副作用更少。这种天然化合物的生物利用度差和代谢快，需要新的研究方法来提高它们在生物体中的稳定性。一种提高类姜黄素效率的合成方法是通过β-二羰基部分将它们与金属配位。我们报告了钌 (II )配合物1-4对人类卵巢癌 A2780 的合成和生物学尝试，含有姜黄素配体。复合物1-4的细胞毒性证明了它们的抗增殖能力，通过主成分分析 (PCA) 确定了 IC 50值与 NF- κ B 转录因子、FGF-2 和 MMP-9 水平之间的相关性。

  DOI：

  10.3390/molecules27144565
• 作为产物：
  描述：

  乙酰丙酮 、 丁香醛 在 盐酸 、 boron trioxide 、 硼酸三丁酯 、 正丁胺 作用下， 生成 (1E,6E)-1,7-bis(4-hydroxy-3,5-dimethoxyphenyl)hepta-1,6-diene-3,5-dione
  参考文献：
  名称：

  含有姜黄素配体的抗增殖钌复合物在人卵巢肿瘤细胞系 A2780 上进行了体外测试，发现它们调节 NF-κB 转录因子、FGF-2 生长因子和 MMP-9 通路的能力

  摘要：

  到目前为止，姜黄的多酚成分已显示出对包括肿瘤疾病在内的多种疾病的显着药理预防活性。这种类型的天然产物可能对抑制癌细胞增殖非常感兴趣，与经典化疗药物相比，副作用更少。这种天然化合物的生物利用度差和代谢快，需要新的研究方法来提高它们在生物体中的稳定性。一种提高类姜黄素效率的合成方法是通过β-二羰基部分将它们与金属配位。我们报告了钌 (II )配合物1-4对人类卵巢癌 A2780 的合成和生物学尝试，含有姜黄素配体。复合物1-4的细胞毒性证明了它们的抗增殖能力，通过主成分分析 (PCA) 确定了 IC 50值与 NF- κ B 转录因子、FGF-2 和 MMP-9 水平之间的相关性。

  DOI：

  10.3390/molecules27144565

文献信息

• Synthesis of Curcumin Analogues as Potential Antioxidant, Cancer Chemopreventive Agents
  作者：Khairia M. Youssef、Magda A. El-Sherbeny、Faiza S. El-Shafie、Hassan A. Farag、Omar A. Al-Deeb、Sit Albanat A. Awadalla

  DOI：10.1002/ardp.200300763

  日期：2004.1

  New series of 3, 5‐bis(substituted benzylidene)‐4‐piperidones, 2, 7‐bis(substituted benzylidene)cycloheptanones, 1, 5‐bis(substituted phenyl)‐1, 4‐pentadien‐3‐ones, 1, 7‐bis(substituted phenyl)‐1, 6‐heptadien‐3, 5‐diones, 1, 1‐bis(substituted cinnamoyl)‐cyclopentanes, and 1, 1‐bis(substituted cinnamoyl)cyclohexanes have been synthesized and tested for their antioxidant activity. Among the tested compounds

  新系列 3, 5-双（取代苯亚甲基）-4-哌啶酮，2, 7-双（取代苯亚甲基）环庚酮，1, 5-双（取代苯基）-1，4-戊二烯-3-，1， 7-双（取代苯基）-1, 6-庚二烯-3, 5-二酮，1, 1-双（取代肉桂酰基）-环戊烷和1, 1-双（取代肉桂酰基）环己烷已合成并测试其性能抗氧化活性。在被测化合物中，化合物II4、II9、II10、II11、V1和V4表现出较高的自由基清除活性，%抑制率分别为90.71、91.24、96.91、94.26、99.23和99.85%。此外，化合物 V1 是外周多核中性粒细胞 (PMN) 的安全成员，存活率为 91%。报告了详细的合成、光谱和生物学数据。
• Antioxidant capacity of curcumin-directed analogues: Structure–activity relationship and influence of microenvironment
  作者：Ya-Jing Shang、Xiao-Ling Jin、Xian-Ling Shang、Jiang-Jiang Tang、Guo-Yun Liu、Fang Dai、Yi-Ping Qian、Gui-Juan Fan、Qiang Liu、Bo Zhou

  DOI：10.1016/j.foodchem.2009.09.024

  日期：2010.4

  Curcumin is the active ingredient of turmeric powder with a variety of biological activities including anti-oxidative activity. In order to find more active antioxidants with curcumin as the lead compound we synthesised a series of enone analogues of curcumin. The present work studied and compared the capacity of curcumin-directed analogues to scavenge 2,2-diphenyl-1-picrylhydrazyl (DPPH center dot) and protect human red blood cells (RBCs) from oxidative haemolysis. It was found that these compounds which bear o-diphenoxyl and o-dimethoxyphenoxyl groups exhibited significantly higher DPPH center dot-scavenging and anti-haemolysis activities than those which bear no such groups. In contrast to curcumin analogues that retained the 7-carbon spacer, the compounds with a 5-carbon linker had lower activity. in the case of the latter, the introduction of a ring further decreased DPPH center dot-scavenging activity. However, the introduction of a ring did increase anti-haemolysis activity, suggesting that the lipophilicity of these compounds might play an important role in the antioxidant activity. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of polyhydroxycurcuminoids
  作者：Somepalli Venkateswarlu、Marellapudi S. Ramachandra、Gottumukkala V. Subbaraju

  DOI：10.1016/j.bmc.2005.06.050

  日期：2005.12

  A series of curcurnin analogs (1-3, 5a-5t) was synthesized through the condensation of appropriately protected hydroxy-benzaldehydes with acetylacetone, followed by deprotection. The antioxidant activity of these analogs was determined by superoxide free radical nitroblue tetrazolium and DPPH free radical scavenging methods and the polyhydroxycurcuminoids (5l-5s) displayed excellent antioxidant activity. These analogs showed cytotoxicity to lymphocytes and promising tumor-reducing activity on Dalton's lymphoma ascites tumor cells. (c) 2005 Elsevier Ltd. All rights reserved.
• CURCUMIN ANALOG COMPOSITIONS AND RELATED METHODS
  申请人：Chen Danyang

  公开号：US20100216859A1

  公开（公告）日：2010-08-26

  Novel curcumin-analog compounds are disclosed that are antioxidants useful in inhibition of pro-inflammation, angiogenic, and vascular permeability factors and elimination of reactive oxygen species. The curcumin compounds specifically inhibit VEGF and are useful in treating various diseases that are mediated through the oxidative stress pathway, including those that are characterized by inflammation, angiogenesis, or vascular leakage.
• COMPOSITIONS AND METHODS FOR DETECTING AMYLOID-BETA-DEGRADING ENZYME ACTIVITY
  申请人：Chen Rita P.-Y.

  公开号：US20130102498A1

  公开（公告）日：2013-04-25

  Novel substrates for detection of activity of amyloid beta degrading enzyme, such as Neprilysin (NEP) and insulin degrading enzyme (IDE), associated with Alzheimer's disease, are provided. A quenched fluorogenic peptide substrate containing the first seven residues of the Aβpeptide plus a C-terminal Cys residue to detect neprilysin activity with a fluorophore attached to the C-terminal Cys and a quencher linked to the N-terminus of the peptide is disclosed. An assay system sensitive to endopeptidase activity of NEP and IDE, but insensitive to other Aβ-degrading enzymes is disclosed. Active compounds are identified by a cell-based assay system for high-throughput screening.