(1E,6E)-4-[(4-hydroxyphenyl)methylidene]-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione | 1028459-90-6

• 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)-4-[(4-hydroxyphenyl)methylidene]-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
• 英文别名: 4-(4-hydroxybenzylidene)-bis-(hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione；4-(4-Hydroxybenzylidene) curcumin；(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxyphenyl)methylidene]hepta-1,6-diene-3,5-dione
• CAS: 1028459-90-6
• 化学式: C₂₈H₂₄O₇
• 分子量: 472.494
• InChiKey: PNCPVSYJULULSS-YDWXAUTNSA-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-[(4-hydroxyphenyl)methylidene]-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione 以 甲醇 、 水 为溶剂， 反应 27.0h， 生成 N'-[(E)-[(1E,5E,6E)-5-[(Z)-[amino(hydroxy)methylidene]hydrazinylidene]-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxyphenyl)methylidene]hepta-1,6-dien-3-ylidene]amino]carbamimidic acid;ruthenium(3+);trichloride
  参考文献：
  名称：

  Synthesis, DNA binding, hemolytic, and anti-cancer assays of curcumin I-based ligands and their ruthenium(III) complexes

  摘要：

  Knoevenagel condensates of curcumin I were synthesized with p-hydroxybenzaldehyde and 4-hydroxy-3,5-dimethoxy benzaldehyde and allowed to react with semicarbazide to form the corresponding curcumin I-based ligands. The ligands were complexed with ruthenium(III) metal ions. These complexes (C-1 and C-2) were purified by chromatography and characterized as octahedral geometries by analytical techniques. The binding affinities of these compounds for calf thymus DNA were determined. DNA binding constants (K (b) ) for the two complexes were 1.46 x 10(4) and 3.54 x 10(4) M-1, respectively. Similarly, the binding constants (K (sv)) for C-1 and C-2 were 9.40 x 10(3) and 9.30 x 10(3) M-1, respectively. Hemolytic assays of the compounds showed less toxicity than the standard anti-cancer drug letrazole. The compounds showed good activity against the cervical cancer cell line (HeLa) and moderate activity against liver hepatocellular carcinoma (HepG2), breast cancer (MDA-MB-231) and human colon adenocarcinoma (HT-29) cells lines. These compounds showed potential for treatment of cervical cancer in the future.

  DOI：

  10.1007/s00044-012-0133-8
• 作为产物：
  描述：

  姜黄素 、 对羟基苯甲醛 在 sodium tetraborate decahydrate 作用下， 以 乙醇 、 水 为溶剂， 以76 %的产率得到(1E,6E)-4-[(4-hydroxyphenyl)methylidene]-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
  参考文献：
  名称：

  作为潜在糖水解酶消化酶抑制剂的新型天然亚芳基姜黄素的合成、体外和体内研究

  摘要：

  糖尿病是人类最常见的代谢性疾病之一，使用草药抑制碳水化合物水解酶、降低血糖具有重要的临床意义...

  DOI：

  10.1080/07391102.2023.2175372

文献信息

• 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 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.
• Synthesis, DNA binding, hemolytic, and anti-cancer assays of curcumin I-based ligands and their ruthenium(III) complexes
  作者：Imran Ali、Kishwar Saleem、Diana Wesselinova、Ashanul Haque

  DOI：10.1007/s00044-012-0133-8

  日期：2013.3

  Knoevenagel condensates of curcumin I were synthesized with p-hydroxybenzaldehyde and 4-hydroxy-3,5-dimethoxy benzaldehyde and allowed to react with semicarbazide to form the corresponding curcumin I-based ligands. The ligands were complexed with ruthenium(III) metal ions. These complexes (C-1 and C-2) were purified by chromatography and characterized as octahedral geometries by analytical techniques. The binding affinities of these compounds for calf thymus DNA were determined. DNA binding constants (K (b) ) for the two complexes were 1.46 x 10(4) and 3.54 x 10(4) M-1, respectively. Similarly, the binding constants (K (sv)) for C-1 and C-2 were 9.40 x 10(3) and 9.30 x 10(3) M-1, respectively. Hemolytic assays of the compounds showed less toxicity than the standard anti-cancer drug letrazole. The compounds showed good activity against the cervical cancer cell line (HeLa) and moderate activity against liver hepatocellular carcinoma (HepG2), breast cancer (MDA-MB-231) and human colon adenocarcinoma (HT-29) cells lines. These compounds showed potential for treatment of cervical cancer in the future.