(1E,6E)-4-benzylidene-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

• 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)-4-benzylidene-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
• 英文别名: 4-Benzylidene curcumin
• 化学式: C₂₈H₂₄O₆
• 分子量: 456.495
• InChiKey: MHUKQIHYJHGFKT-QHKWOANTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1E,6E)-4-benzylidene-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  In silico and biological exploration of greenly synthesized curcumin-incorporated isoniazid Schiff base and its ruthenium complexes

  摘要：

  本研究以具有生物活性的姜黄素和不同的醛为原料，通过超声波介导制备了三种 Knoevenagel 缩合物。通过这些 Knoevenagel 缩合物与异烟肼反应，制备出姜黄素席夫碱。通过各种分析技术，如元素分析、摩尔电导测量和光谱技术，如紫外可见光、傅立叶变换红外光谱、核磁共振、电子发射光谱和电离质谱，合成了钌席夫碱配合物，并确认了这些配合物的八面体几何形状。此外，还使用 Gaussian 09 W 软件进行了几何优化和 DFT 计算，并对这些复合物进行了量子力学计算。使用 SWISS ADME、PASS 在线和 molinspiration 在线软件对合成化合物的药代动力学行为进行了研究。在此基础上，进行了体内和体外药物研究，发现所有配合物都比配体具有更强的生物活性。所有合成的化合物都与 1BNA 和 4fm9 结肠癌受体对接。有趣的是，通过对 CT-DNA 进行紫外可见吸收滴定和粘度测量，证实了合成化合物的插层结合功效。

  DOI：

  10.1007/s11224-022-02065-0
• 作为产物：
  描述：

  姜黄素 、 苯甲醛 在 哌啶 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以87%的产率得到(1E,6E)-4-benzylidene-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
  参考文献：
  名称：

  姜黄素衍生物的结构活性关系，细胞毒性和抗氧化活性的评估。

  摘要：

  设计了一系列姜黄素衍生物/类似物，并描述了其合成的有效方法。筛选所有合成的化合物的细胞毒性并评估其抗氧化活性。已经通过MTT测定法评估了针对三种细胞系Hep-G2，HCT-116和QG-56的细胞毒性作用。结构活性关系表明，特别是化合物3c（IC50值为6.25μM）对三种细胞系表现出更好的细胞毒性作用。根据SAR研究的结果，发现4H-嘧啶并[2,1-b]苯并噻唑衍生物（2e和2f），吡唑（3a，3b，3c和3d）亚苄基（4d）具有比姜黄素更好的抗氧化活性。

  DOI：

  10.1016/j.bmcl.2015.12.013

文献信息

• Biological evaluation of a novel amino acid-based macrocyclic Mn(III) and Fe(III) complexes
  作者：C. Joel、R. Biju Bennie、S. Daniel Abraham、S. Iyyam Pillai、S. Theodore David

  DOI：10.1002/aoc.4516

  日期：2018.11

  oxyphenyl)hepta‐1,6‐diene‐3,5‐bis(2‐imino‐3‐phenylpropanoic acid) of the type N2O2 has been synthesized from curcumin derived non‐enolisable diketone and L‐phenylalanine and complexed with Mn(III) and Fe(III) metal ions. The non‐enolisable curcumin was obtained by Knoevenagel condensation. The synthesized ligand and complexes (MnL & FeL) were characterized by various spectral techniques. Using absorption

  一种新的N 2型四齿配体4-苄基-1,7-双（4-羟基-3-甲氧基苯基）庚-1,6-二烯-3,5-双（2-亚氨基-3-苯基丙酸）Ø 2由姜黄素衍生的不可烯丙基二酮和L-苯丙氨酸合成，并与Mn（III）和Fe（III）金属离子络合。不可烯醇化姜黄素是通过Knoevenagel缩合获得的。通过各种光谱技术对合成的配体和配合物（MnL和FeL）进行了表征。使用吸收和发射光谱技术已经进行了CT‐DNA和BSA结合研究。吸收和发射光谱工具揭示了CT‐DNA与金属络合物之间的结合结合模式。通过金属络合物将BSA的荧光猝灭在340 nm附近，然后进行静态猝灭机理。在三个不同的温度下记录了BSA的发射光谱。结合位点，结合方式，结合能和供体-受体距离基于Forster' 计算出共振能量转移（FRET）。为了证实实验结果，已经通过分子对接研究讨论了金属络合物与CT-DNA和BSA的结合位点。
• Ghosh, Journal of the Chemical Society, 1919, vol. 115, p. 299
  作者：Ghosh

  DOI：——

  日期：——
• Synthesis and evaluation of antimicrobial activity of 4H-pyrimido[2,1-b]benzothiazole, pyrazole and benzylidene derivatives of curcumin
  作者：Pramod K. Sahu、Praveen K. Sahu、S.K. Gupta、D. Thavaselvam、D.D. Agarwal

  DOI：10.1016/j.ejmech.2012.05.020

  日期：2012.8

  A novel, one-pot, simple, efficient procedure for 4H-pyrimido[2,1-b]benzothiazole (4a-h), pyrazole (6a-d) and benzylidene (7a-d) derivatives of curcumin under solvent and solvent free conditions in microwave with good yield is have been synthesized. The synthesized compounds were evaluated for their antibacterial activity against gram-positive and gram-negative bacteria viz. Staphylococcus aureus, Pseudomonas aeruginosa, Salmonella typhi, Escherichia coli, Bacillus cereus and Providencia rettgeri and antifungal activity against fungi viz Aspergillus niger, Aspergillus fumigates, Aspergillus flavus. Detailed mechanistic study shows reaction proceeds through Knoevenagel type intermediate 3a which has been suggested as key intermediate for reaction (Fig. 3). (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis and exploration of novel curcumin analogues as anti-malarial agents
  作者：Satyendra Mishra、Krishanpal Karmodiya、Namita Surolia、Avadhesha Surolia

  DOI：10.1016/j.bmc.2007.12.054

  日期：2008.3.15

  Curcumin, a major yellow pigment and active component of turmeric, has been shown to possess anti-inflammatory and anti-cancer activities. Recent studies have indicated that curcumin inhibits chloroquine-sensitive (CQ-S) and chloroquine-resistant (CQ-R) Plasmodium falciparum growth in culture with an IC50 of similar to 3.25 mu M (MIC = 13.2 mu M) and IC50 4.21 mu M (MIC = 14.4 mu M), respectively. In order to expand their potential as anti-malarials a series of novel curcumin derivatives were synthesized and evaluated for their ability to inhibit P. falciparum growth in culture. Several curcumin analogues examined show more effective inhibition of P. falciparum growth than curcumin. The most potent curcumin compounds 3, 6, and 11 were inhibitory for CQ-S P. falciparum at IC50 of 0.48, 0.87, 0.92 mu M and CQ-R P. falcipartan at IC50 of 0.45 mu M, 0.89, 0.75 mu M, respectively. Pyrazole analogue of curcumin (3) exhibited sevenfold higher anti-malarial potency against CQ-S and ninefold higher anti-malarial potency against CQ-R. Curcumin analogues described here represent a novel class of highly selective P. falcipartan inhibitors and promising candidates for the design of novel anti-malarial agents. (C) 2007 Elsevier Ltd. All rights reserved.
• Antioxidant activity and electrochemical elucidation of the enigmatic redox behavior of curcumin and its structurally modified analogues
  作者：Niki S. Jha、Satyendra Mishra、Shailendra K. Jha、Avadhesha Surolia

  DOI：10.1016/j.electacta.2014.11.026

  日期：2015.1

  Here, we report studies on the antioxidant activity and redox behavior of curcumin and its structurally modified synthetic analogues. We have synthesized a number of analogues of curcumin which abrogate its keto-enol tautomerism or substitute the methylene group at the centre of its heptadione moiety implicated in the hydride transfer and studied their redox property. From cyclic voltammetric studies, it is demonstrated that H-atom transfer from CH2 group at the center of the heptadione link also plays an important role in the antioxidant properties of curcumin along with that of its phenolic -OH group. In addition, we also show that the conversion of 1, 3-dicarbonyl moiety of curcumin to an isosteric heterocycle as in pyrazole curcumin, which decreases its rotational freedom, leads to an improvement of its redox properties as well as its antioxidant activity. (C) 2014 Elsevier Ltd. All rights reserved.