5-hydroxy-1,7-diphenylhepta-1,4,6-trien-3-one | 98885-82-6

• 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: 5-hydroxy-1,7-diphenylhepta-1,4,6-trien-3-one
• 英文别名: 1,7-diphenylhepta-1,6-diene-3,5-dione；3-hydroxy-1t.7t-diphenyl-heptatrien-(1.3ξ.6)-one-(5)；3-Hydroxy-1t.7t-diphenyl-heptatrien-(1.3ξ.6)-on-(5)；(1E,6E)-5-hydroxy-1,7-diphenylhepta-1,4,6-trien-3-one
• CAS: 98885-82-6
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: DMZJFBKOUHBFQM-NHGJSFOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-hydroxy-1,7-diphenylhepta-1,4,6-trien-3-one 在 盐酸羟胺 、 溶剂黄146 作用下， 以83%的产率得到3,5-bis(styryl)isoxazole
  参考文献：
  名称：

  姜黄素衍生的3,5-双（苯乙烯基）异恶唑-机械化学合成和抗氧化活性

  摘要：

  姜黄素衍生的3,5-双（苯乙烯基）异恶唑的机械化学合成及其抗氧化活性已有报道。 姜黄素衍生的3,5-双（苯乙烯基）异恶唑（4a-g）的机械化学合成及其抗氧化活性已有报道。

  DOI：

  10.1007/s12039-016-1119-8
• 作为产物：
  描述：

  以 甲醇 、 二甲基亚砜 为溶剂， 生成 5-hydroxy-1,7-diphenylhepta-1,4,6-trien-3-one
  参考文献：
  名称：

  一些二芳基庚烷的合成、结构、光物理性质和DFT研究

  摘要：

  在目前的工作中，我们描述了一些姜黄素类二芳基庚烷的结构、光物理性质和 DFT 计算（4a-c）。这些化合物通过多光谱技术进行表征，包括中间体之一的 X 射线单晶 ( 3a）。分子几何和结构特征通过 DFT -B3LYP/6-31G(d,p) 计算进行配置；然而，在溴和碘衍生物的情况下，使用组合的 6-31G(d,p)/LANL2Dz 基组 (B3LYP/Gen)。与天然姜黄素相比，这些二芳基庚烷在溶液中表现出蓝移的光谱特征；还注意到聚集增强的发射特性。卤原子的加入增强了化合物的热稳定性。在计算波数的笛卡尔坐标位移的帮助下，我们为观察到的红外基本原理提出了可靠的振动分配。这项研究的结果将为越来越多的关于姜黄素特性的研究提供有价值的补充。

  DOI：

  10.1016/j.molstruc.2022.133254

文献信息

• A New Family of Homoleptic Copper Complexes of Curcuminoids: Synthesis, Characterization and Biological Properties
  作者：William Meza-Morales、Juan Machado-Rodriguez、Yair Alvarez-Ricardo、Marco Obregón-Mendoza、Antonio Nieto-Camacho、Rubén. Toscano、Manuel Soriano-García、Julia Cassani、Raúl Enríquez

  DOI：10.3390/molecules24050910

  日期：——

  in the number of known crystal structures of homoleptic metal complexes of curcuminoids revealing more favorable crystallinity. The crystal structures of the present new copper complexes show four-fold coordination with a square planar geometry. Two polymorphs were found for DiBncOC-Cu when crystallized from DMF. The characterization of these new complexes was carried out using infrared radiation (IR)

  我们在此报道了五种新的类姜黄素均配铜配合物的合成和晶体结构。类姜黄素均配复合结构报道的稀缺归因于此类衍生物缺乏结晶度，因此，通过单晶 X 射线衍射对其进行表征的情况很少。通过酯化或醚化抑制酚类相互作用的配体设计显着增加了类姜黄素均配金属配合物的已知晶体结构的数量，揭示了更有利的结晶度。目前的新型铜配合物的晶体结构显示出具有方形平面几何形状的四重配位。当从 DMF 中结晶时，发现了 DiBncOC-Cu 的两种多晶型物。使用红外辐射（IR）、核磁共振（NMR）、电子顺磁共振（EPR）和单晶X射线衍射（SCXRD）对这些新配合物进行了表征，并对所得配合物的抗氧化和细胞毒活性进行了表征。被评价。
• Synthesis, characterization, cytotoxic activity of half-sandwich rhodium(III), and iridium(III) complexes with curcuminoids
  作者：Wei Su、Xiaohui Wang、Xiaolin Lei、Qi Xiao、Shan Huang、Peiyuan Li

  DOI：10.1016/j.jorganchem.2017.01.028

  日期：2017.3

  A series of organometallic rhodium and iridium complexes with curcuminoid ligands (1–14) have been synthesized and characterized by NMR, IR, elemental analysis, and HR-ESI-mass spectrometry. The molecular structure of complex 9 has been characterized by X-ray crystallography. The in vitro activity of all the compounds has been evaluated against the HepG2, HeLa human cancer cell lines and HEK-293T human

  一系列有机金属铑和铱配合物类姜黄素配体（的1 - 14）已经被合成和表征通过NMR，IR，元素分析，和HR-ESI-MS分析。配合物9的分子结构已经通过X射线晶体学表征。在体外的所有化合物的活性已靠着HepG2细胞，HELA人癌细胞系和HEK-293T人类健康的细胞系进行了评价。铑配合物6表现出优异的抗癌活性和对癌细胞系的有希望的选择性。此外，电泳迁移率谱研究紧随6与DNA的相互作用。
• Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway
  作者：Pay-Chin Leow、Priti Bahety、Choon Pei Boon、Chong Yew Lee、Kheng Lin Tan、Tianming Yang、Pui-Lai Rachel Ee

  DOI：10.1016/j.ejmech.2013.10.073

  日期：2014.1

  Osteosarcoma is a primary bone malignancy with aggressive metastatic potential and poor prognosis rates. In our earlier work we have investigated the therapeutic potential of curcumin as an anti-invasive agent in osteosarcoma by its ability to regulate the Wnt/beta-catenin signaling pathway. However, the clinical use of curcumin is limited owing to its low potency and poor pharmacokinetic profile. In this study, an attempt was made to achieve more potent Wnt inhibitory activity in osteosarcoma cells by carrying out synthetic chemical modifications of curcumin. We synthesized a total of five series consisting of 43 curcumin analogs and screened in HEK293T cells for inhibition of beta-catenin transcriptional activity. Six promising analogs, which were 6.5- to 60-fold more potent than curcumin in inhibiting Wnt activity, were further assessed for their anti-invasive activity and Wnt inhibitory mechanisms. Western blot analysis showed disruption of beta-catenin protein nuclear translocation following treatment with analogs 2f, 3c and 4f. Using transwell assays, we also found that these compounds were more potent than la (curcumin) in impeding the invasion of osteosarcoma cells, possibly through suppressing MMP-9 activity. Structure-activity-relationship studies revealed that Wnt inhibitory effects could be enhanced by shortening and restraining the flexibility of the 7-carbon linker moiety connecting the terminal aromatic rings of curcumin and substituting both rings with appropriate substituents. Our results demonstrate that the synthesized curcumin analogs are more potent Wnt inhibitors in osteosarcoma cell lines as compared to parental curcumin and are good lead compounds for further development. Future in vivo tests with these compounds will define their therapeutic potentials as promising drug candidates for clinical treatment of osteosarcoma. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Antibacterial activity of 3,3′-dihydroxycurcumin (DHC) is associated with membrane perturbation
  作者：Carlos R. Polaquini、Luana G. Morão、Ana C. Nazaré、Guilherme S. Torrezan、Guilherme Dilarri、Lúcia B. Cavalca、Débora L. Campos、Isabel C. Silva、Jessé A. Pereira、Dirk-Jan Scheffers、Cristiane Duque、Fernando R. Pavan、Henrique Ferreira、Luis O. Regasini

  DOI：10.1016/j.bioorg.2019.103031

  日期：2019.9

  Curcumin is a plant diphenylheptanoid and has been investigated for its antibacterial activity. However, the therapeutic uses of this compound are limited due to its chemical instability. In this work, we evaluated the antimicrobial activity of diphenylheptanoids derived from curcumin against Gram-positive and Gram-negative bacteria, and also against Mycobacterium tuberculosis in terms of MIC (Minimum Inhibitory Concentration) and MBC (Minimum Bactericidal Concentration) values. 3,3'-Dihydroxycurcumin (DHC) displayed activity against Enterococcus faecalis, Staphylococcus aureus and M. tuberculosis, demonstrating MIC values of 78 and 156 mu g/mL. In addition, DHC was more stable than curcumin in acetate buffer (pH 5.0) and phosphate buffer (pH 7.4) for 24 h at 37 degrees C. We proposed that membrane and the cell division protein FtsZ could be the targets for DHC due to that fact that curcumin exhibits this mode of antibacterial action. Fluorescence microscopy of Bacillus subtilis stained with SYTO9 and propidium iodide fluorophores indicated that DHC has the ability to perturb the bacterial membrane. On the other hand, DHC showed a weak inhibition of the GTPase activity of B. subtilis FtsZ. Toxicity assay using human cells indicated that DHC has moderate capacity to reduce viability of liver cells (HepG2 line) and lung cells (MRC-5 and A549 lines) when compared with doxorubicin. Alkaline comet assay indicated that DHC was not able to induce DNA damage in A549 cell line. These results indicated that DHC is promising compound with antibacterial and antitubercular activities.
• Borsche; Lewinsohn, Chemische Berichte, 1933, vol. 66, p. 1792,1796
  作者：Borsche、Lewinsohn

  DOI：——

  日期：——