(1E,6E)-4-(4-dimethylamino)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-(4-dimethylamino)benzylidene-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
• 英文别名: 4-[4-(dimethylamino)benzylidene]-1,7-bis-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione；(1E,6E)-4-[(4-dimethylaminophenyl)methylene]-1,7-bis(4-hydroxy-3-methoxy-phenyl)hepta-1,6-diene-3,5-dione；(1E,6E)-4-[[4-(dimethylamino)phenyl]methylidene]-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
• 化学式: C₃₀H₂₉NO₆
• 分子量: 499.563
• InChiKey: BOUYSULZWXCTKG-FNCQTZNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  96.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  姜黄素 、 对二甲氨基苯甲醛 在 三苯基膦 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以60.2%的产率得到(1E,6E)-4-(4-dimethylamino)benzylidene-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
  参考文献：
  名称：

  Synthesis, Characterization and Antioxidant Studies of Curcumin Derivatives

  摘要：

  成功合成了三种具有活性亚甲基（1、3）和酮基（2）修饰的姜黄素衍生物，并通过 1H NMR 和 FT-IR 光谱技术进行了表征。姜黄素活性亚甲基位点上的取代增加了抗氧化行为，但由于羰基的修饰而降低了抗氧化行为。观察到的结果表明结构修饰将有助于调整姜黄素的抗氧化行为。比较具有强供体基团的化合物1比化合物3，前者表现出更高的清除活性。这意味着给电子强度在决定抗氧化活性方面也起着重要作用。观察到的结果将有助于开发新的姜黄素衍生物，以获得更好的抗氧化性能。

  DOI：

  10.14233/ajchem.2015.18529

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。
• Synthesis, Characterization and Antioxidant Studies of Curcumin Derivatives
  作者：R. Revathi、D. Arul Ananth、A. Rameshkumar、T. Sivasudha

  DOI：10.14233/ajchem.2015.18529

  日期：——

  Three curcumin derivatives having modification in active methylene group (1, 3) and keto groups (2) were successfully synthesized and characterized by 1H NMR and FT-IR spectroscopic techniques. The substitution on the active methylene site of curcumin increases the antioxidant behaviour but it is decreased on modifications in the carbonyl group. The observed results suggest that the structural modifications will help in tuning the antioxidant behaviour of curcumin. While comparing compound 1 which have strong donating group than compound 3, the former shows higher scavenging activity. This implies the electron donating strength also plays an important role in determining the antioxidant activity. The observed results will aid in developing new curcumin derivatives for better antioxidant properties.

  成功合成了三种具有活性亚甲基（1、3）和酮基（2）修饰的姜黄素衍生物，并通过 1H NMR 和 FT-IR 光谱技术进行了表征。姜黄素活性亚甲基位点上的取代增加了抗氧化行为，但由于羰基的修饰而降低了抗氧化行为。观察到的结果表明结构修饰将有助于调整姜黄素的抗氧化行为。比较具有强供体基团的化合物1比化合物3，前者表现出更高的清除活性。这意味着给电子强度在决定抗氧化活性方面也起着重要作用。观察到的结果将有助于开发新的姜黄素衍生物，以获得更好的抗氧化性能。
• 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.