4,4'-diacetyl curcumin | 297179-80-7

• 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: 4,4'-diacetyl curcumin
• 英文别名: 1,7-bis(4-(acetyloxy)-3-methoxyphenyl)-1,6-Heptadiene-3,5-dione；[4-[7-(4-acetyloxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dienyl]-2-methoxyphenyl] acetate
• CAS: 297179-80-7
• 化学式: C₂₅H₂₄O₈
• 分子量: 452.461
• InChiKey: GQRYDKSIXWXTSH-UHFFFAOYSA-N

物化性质

• 沸点：
  595.4±50.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4,4'-diacetyl curcumin 在 4-二甲氨基吡啶 、 potassium carbonate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成
  参考文献：
  名称：

  Chitosan nano-vehicles as biocompatible delivering tools for a new Ag(I)curcuminoid-Gboxin analog complex in cancer and inflammation therapy

  摘要：

  A novel anticancer and anti-inflammatory agent based on hybrid curcuminoid-Gboxin analog (FLLL49-GbA) and its macromolecular silver(I) complex (Ag(I)FLLL49-GbA) have successfully synthesized. In addition, chitosan nanoparticles (CNPs) were used to encapsulate this macromolecular complex, targeting enhancing its therapeutic effect and minimizing its side impacts. The encapsulated Ag(I) complex was significantly triggered apoptosis (P < 0.05) with much more rapidly release of Ag(I)FLLL49-GbA from the CNPs at pH 5.3 than at pH 7.4, which is beneficial for cancer-targeted drug delivery. Free complex showed promising ability in preventing glucose uptake and lactate production coupled with cellular ATP depletion in cancer cells. Additionally, there was significant decrease in the inflammatory cytokines in breast cancer (MCF-7) and lung cancer (A549) cells with values of P < 0.01 and P < 0.001 after 24 h incubation. Furthermore, the death-inducing proteins have been significantly up-regulated (P < 0.01 to P < 0.001) after 36 h incubation of cancer cells. Consequently, the novel curcuminoid macromolecule showed significant feasibility in triggering the high expression of apoptotic caspases caspase 3, caspase 8, P53, and Bax (P < 0.01 to P < 0.001) after 48 h of chemotherapy. Noteworthy, the cytotoxicity of Ag(I)FLLL49-GbA was significantly increased toward cancer cells (MCF-7 > A549), while, reduced toward normal cells (HeLa) after loading on chitosan Nano-vehicles.

  DOI：

  10.1016/j.ijbiomac.2020.10.153
• 作为产物：
  描述：

  curcumin 、 乙酸酐 在 吡啶 作用下， 反应 4.0h， 以90%的产率得到4,4'-diacetyl curcumin
  参考文献：
  名称：

  [EN] ANTI-QUORUM SENSING, ANTI-BIOFILM, AND INFLAMMATION ATTENUATING COMPOUNDS, COMPOSITIONS, AND METHODS OF USING SAME
  [FR] COMPOSÉS DE DÉTECTION ANTI-QUORUM, ANTI-BIOFILM, ET COMPOSÉS ATTÉNUANT L'INFLAMMATION, COMPOSITIONS ET LEURS MÉTHODES D'UTILISATION

  摘要：

  本发明涉及具有抗群体感应活性、抗炎活性或两者的化合物，包括这些化合物的组合物以及使用它们的方法，例如用于治疗患有疾病的受试者。

  公开号：

  WO2022153306A1

文献信息

• Synthesis of novel curcuminoids accommodating a central β-enaminone motif and their impact on cell growth and oxidative stress
  作者：Rob De Vreese、Charlotte Grootaert、Sander D’hoore、Atiruj Theppawong、Sam Van Damme、Maarten Van Bogaert、John Van Camp、Matthias D’hooghe

  DOI：10.1016/j.ejmech.2016.07.017

  日期：2016.11

  solubility and chemical anti-oxidant properties, and were applied in screening assays for cell toxicity, growth and oxidative stress using CHO-K1, EA.hy926, HT-29 and Caco-2 cell lines. Compared to native curcumin, many nitrogen derivatives showed a stronger antiproliferative effect, which was highly structure and cell type dependent. In addition, the correlation between cell viability and reactive oxygen

  姜黄素是靶向重要信号通路的多种成分而没有毒性的高潜力药物，因此被认为是药物化学中有价值的先导结构。不幸的是，由于生物利用度低（部分）与不稳定的β-二酮结构有关，大多数姜黄素不能很好地发挥作用。在这方面，带有中央β-烯胺酮片段的姜黄素衍生物可以具有改善的溶解度和肠稳定性，因此可以代表具有更高生物活性的一类新的类似物。在这种心态下，十三N通过使用蒙脱石K10粘土和微波辐照的新方法，可以有效地合成α-烷基烯胺酮。然后根据溶解度和化学抗氧化特性对这些化合物进行表征，并使用CHO-K1，EA.hy926，HT-29和Caco-2细胞系将其用于细胞毒性，生长和氧化应激的筛选测定。与天然姜黄素相比，许多氮衍生物显示出更强的抗增殖作用，其高度依赖于结构和细胞类型。此外，细胞活力与活性氧产生之间的相关性受到限制。因此，这组新的姜黄素衍生物可能有助于阐明与氧化应激相关疾病的其他机制，并最终用作天然姜黄素的更多生物利用度和生物活性替代物。
• Syntheses, Structures, and Bioactivities Evaluation of some Transition Metal Complexes with 4,4'-Diacetylcurcumin
  作者：Chien Thang Pham、Thu Thuy Pham、Hung Huy Nguyen、Thi Nguyet Trieu

  DOI：10.1002/zaac.202000088

  日期：2020.6.30

  transition metal ions, namely Fe3+, Co2+, Ni2+ and Zn2+, in methanol result in the corresponding homoleptic metal complexes. All the obtained complexes were characterized by elemental analysis, high resolution mass spectrometry, IR spectroscopy, magnetic moment and single‐crystal X‐ray diffraction. Structural analyses are unprecedentedly performed for the FeIII, CoII, and NiII complexes and reveal

  4,4'-二乙酰姜黄素（HL）与一系列过渡金属离子（即Fe 3+，Co 2 +，Ni 2+和Zn 2+）在甲醇中的化学计量反应生成相应的均相金属络合物。所有获得的配合物均通过元素分析，高分辨率质谱，红外光谱，磁矩和单晶X射线衍射进行了表征。对Fe III，Co II和Ni II配合物进行了前所未有的结构分析，揭示了具有[Fe（L）3 ]和[M（L）2（MeOH）2 ]组成的八面体单核配合物（M = Co三价和二价金属离子分别为2 +，Ni 2 +，Zn 2+）。在所有复合物中，去质子化的配体都充当具有（O，O）螯合的β-二酮酸酯部分的单阴离子和二齿配体。游离配体HL对人MCF-7乳腺癌和HepG2肝癌细胞具有相当大的抗增殖作用，IC 50值分别为20.91±2.16μg · mL –1和12.85±1.85μg · mL –1。Co II和Zn II配合物的IC 50值为14.53–20.80μg
• Synthesis, cytotoxic and combined cDDP activity of new stable curcumin derivatives
  作者：Erika Ferrari、Sandra Lazzari、Gaetano Marverti、Francesca Pignedoli、Ferdinando Spagnolo、Monica Saladini

  DOI：10.1016/j.bmc.2009.03.016

  日期：2009.4

  New curcumin derivatives are synthesized in order to improve chemical properties of curcumin. The aromatic ring glycosylation of curcumin provides more water-soluble compounds with a greater kinetic stability which is a fundamental feature for drug bioavailability. The glycosylation reaction is quite simple, low cost, with high yield and minimum waste. NMR data show that the ability of curcumin to coordinate metal ion, in particular Ga(III), is maintained in the synthesized products. Although the binding of glucose to curcumin reduces the cytotoxicity of the derivatives towards cisplatin (cDDP)-sensitive and -resistant human ovarian carcinoma cell lines, the compounds display a good selectivity since they are much less toxic against non-tumourigenic Vero cells. The combination of cDDP with the most active glycosyl-curcuminoid drug against both cDDP-sensitive and -resistant as well as against Vero cell lines is tested. The results show an improvement of cDDP efficacy with higher selectivity towards cancer cells than non-cancer cells. These studies indicate the need for developing new valid components of drug treatment protocols to cDDP-resistant cells as well. (C) 2009 Elsevier Ltd. All rights reserved.
• Ghosh, Journal of the Chemical Society, 1919, vol. 115, p. 299
  作者：Ghosh

  DOI：——

  日期：——
• Jackson; Menke, American Chemical Journal, 1884, vol. 6, p. 78
  作者：Jackson、Menke

  DOI：——

  日期：——