(1E,6E)-4-(2-hydroxybenzylidene)-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-(2-hydroxybenzylidene)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
• 英文别名: (1E,6E)-1,7-bis(4-hydroxy-3-methoxy-phenyl)-4-[(2-hydroxyphenyl)methylene]hepta-1,6-diene-3,5-dione；(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-[(2-hydroxyphenyl)methylidene]hepta-1,6-diene-3,5-dione
• 化学式: C₂₈H₂₄O₇
• 分子量: 472.494
• InChiKey: VNQSGINHYTZUFY-MKICQXMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  35
• 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：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1E,6E)-4-(2-hydroxybenzylidene)-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 、 水杨醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (1E,6E)-4-(2-hydroxybenzylidene)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
  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

文献信息

• Structure activity relationship, cytotoxicity and evaluation of antioxidant activity of curcumin derivatives
  作者：Pramod K. Sahu、Praveen K. Sahu、Puran L. Sahu、Dau D. Agarwal

  DOI：10.1016/j.bmcl.2015.12.013

  日期：2016.2

  compound 3c, (IC50 value 6.25 μM) has shown better cytotoxicity effect against three cell lines. According to results of SAR study, it was found that 4H-pyrimido[2,1-b]benzothiazole derivatives (2e and 2f), pyrazoles (3a, 3b, 3c and 3d) benzylidenes (4d) exhibited better antioxidant activity than curcumin. A correlation of structure and activities relationship of these compounds with respect to drug

  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。
• Novel curcumin analogs targeting TNF-induced NF-κB activation and proliferation in human leukemic KBM-5 cells
  作者：Ajit P. Zambre、V.M. Kulkarni、Subhash Padhye、Santosh K. Sandur、Bharat B. Aggarwal

  DOI：10.1016/j.bmc.2006.06.056

  日期：2006.11

  Novel curcumin analogs were synthesized using Knoevenagel condensation to convert enolic diketones of curcumin into non-enolizable ones and Schiff bases were prepared using a bioactive thiosemicarbazide pharmacophore. Copper(II) conjugates of all synthesized ligands were prepared and structurally characterized as well as evaluated for their potential of inhibiting TNF-induced NF-kappa B activation and proliferation in human leukemic KBM-5 cells wherein compound 13 was found to be more potent than curcumin. Compounds were further examined on other tumor cell lines such as Jurkat, H1299, and MM1, respectively. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.
• Bioactive Derivatives of Curcumin Attenuate Cataract Formation<i>In Vitro</i>
  作者：Asha Radha、Sudha Devi Rukhmini、Sasikala Vilasini、Priya Rajan Sakunthala、Balachandran Sreedharan、Mohanan Puzhavoorparambil Velayudhan、Annie Abraham

  DOI：10.1111/cbdd.12021

  日期：2012.12

  In this study, curcumin derivatives salicylidenecurcumin (CD1) and benzalidenecurcumin (CD2)] were prepared, and their biological activity was compared in in vitro selenite‐induced cataract model. The antioxidant activity was studied using DPPH radical scavenging assay. Knoevenagel condensates of curcumin exhibited higher DPPH radical scavenging activity compared with curcumin. The anticataractogenic potential of curcumin derivatives was analyzed using lens organ culture method. The activity of antioxidant enzymes and calcium homeostasis was reversed to near normal levels following treatment in organ cultured rat lenses. These results indicated that curcumin and its derivatives—CD1 and CD2—are beneficial against selenite‐induced cataract in vitro. Of these, CD1 is having higher bioactive potential compared with curcumin and CD2.
• In silico and biological exploration of greenly synthesized curcumin-incorporated isoniazid Schiff base and its ruthenium complexes
  作者：Porkodi Jeyaraman、Samuel Michael、Raman Natrajan、Anto Arockia Raj Adaikalam

  DOI：10.1007/s11224-022-02065-0

  日期：——

  In the present investigation, ultrasound-mediated three Knoevenagel condensates have been prepared from biologically active curcumin and different aldehydes. Curcumin Schiff bases have been prepared by reacting these Knoevenagel condensates with isoniazid. Ruthenium Schiff base complexes are synthesized and octahedral geometry of these complexes are confirmed by various analytical techniques like elemental analysis, molar conductive measurements, and spectroscopic techniques like UV–Vis, FT-IR, NMR, EPR, and ESI mass. Moreover, optimized geometry and DFT calculation have been done using Gaussian 09 W software and the quantum mechanical calculation of these complexes is also performed. Pharmacokinetic behavior of the synthesized compounds is examined using SWISS ADME, PASS online, and molinspiration online software. Based on this, in vivo and in vitro pharmaceutical investigations are carried out and it is found that all the complexes possess potent biological activity than the ligand. All the synthesized compounds are docked against 1BNA and 4fm9 colon cancer receptors. Interestingly, intercalative binding efficacy of the synthesized compounds is confirmed by using UV–visible absorption titration and viscosity measurements against CT-DNA.

  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。