1,5-二对羟苯基-1,4-戊二烯-3-酮 | 3654-49-7

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 1,5-二对羟苯基-1,4-戊二烯-3-酮
• 英文名称: bis(4-hydroxybenzylidene)acetone
• 英文别名: 1,5-bis(4-hydroxyphenyl)-1,4-pentadiene-3-one；1,5-bis(4-hydroxyphenyl)-1,4-pentadien-3-one；1,5-bis(4-hydroxyphenyl)penta-1,4-dien-3-one；1,5-bis-(4-hydroxy-phenyl)-penta-1,4-dien-3-one；1,5-Bis-(4-hydroxy-phenyl)-penta-1,4-dien-3-on；1,5-bis(4-hydroxyphenyl)penta 1,4-diene-3-one
• CAS: 3654-49-7
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: FTEGUKWEUQPKIS-UHFFFAOYSA-N

物化性质

• 熔点：
  237-238 °C
• 沸点：
  492.7±40.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2914501900
• 储存条件：
  2-8℃

制备方法与用途

化学性质：黄色粉末。

反应信息

• 作为反应物：
  描述：

  1,5-二对羟苯基-1,4-戊二烯-3-酮 在 palladium dichloride 氢碘酸 、 氢气 作用下， 以 溶剂黄146 、 丙酮 为溶剂， 生成 1,5-Bis-(4-hydroxy-phenyl)-pentan
  参考文献：
  名称：

  Spaltungen mittels diazoniumverbindungen und Chinonimidchlorid, 4. Mitt.: �ber Effekte entlang einer ges�ttigten Kohlenstoffkette

  摘要：

  DOI：

  10.1007/bf00913071
• 作为产物：
  描述：

  4-(四氢-吡喃-2-基氧基)-苯甲醛 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 1,5-二对羟苯基-1,4-戊二烯-3-酮
  参考文献：
  名称：

  Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.10.073

文献信息

• Effects of diarylpentanoid analogues of curcumin on chemiluminescence and chemotactic activities of phagocytes
  作者：Ibrahim Jantan、Syed Nasir Abbas Bukhari、Nordin Haji Lajis、Faridah Abas、Lam Kok Wai、Malina Jasamai

  DOI：10.1111/j.2042-7158.2011.01423.x

  日期：2012.2.6

  A series of 43 curcumin diarylpentanoid analogues were synthesized and evaluated for their inhibitory effects on the chemiluminescence and chemotactic activity of phagocytes in vitro.

  The effects of the compounds on the respiratory burst of human whole blood and isolated human polymorphonuclear leukocytes (PMNs) were evaluated using a luminol-based chemiluminescence assay and their effect on chemotactic migration of PMNs was investigated using the Boyden chamber technique.

  Compounds 6, 17, 25 and 30 exhibited significant inhibitory activity on the oxidative burst of PMNs. The presence of methoxy groups at positions 2 and 5, and methoxylation and fluorination at positions 4 and 2 of both phenyl rings, respectively, may contribute significantly to their reactive oxygen species inhibition activity. Compounds 7, 17, 18, 24 and 32 showed strong inhibition of the chemotaxis migration of PMNs. Chlorination at various positions of both phenyl rings of cyclohexanone diarylpentanoid resulted in compounds with potent inhibitory effects on PMN migration.

  The results suggest that some of these diarylpentanoid analogues are able to modulate the innate immune response of phagocytes at different steps, emphasizing their potential as a source of new immunomodulatory agents.

  摘要 目的 合成了一系列43个姜黄素二芳基戊酮类似物，并评估它们对体外吞噬细胞化学发光和趋化活性的抑制作用。 方法 使用基于流明的化学发光测定法评估化合物对人全血和分离的人多形核白细胞（PMNs）呼吸爆发的影响，并利用Boyden室技术研究它们对PMNs趋化迁移的影响。 主要发现 化合物6、17、25和30在PMNs的氧化爆发上表现出显著的抑制活性。在两个苯环的2和5位置有甲氧基基团，以及在4和2位置分别有甲氧化和氟化基团的存在，可能会显著促进它们对活性氧化物种的抑制活性。化合物7、17、18、24和32显示出对PMNs趋化迁移的强烈抑制作用。在环己酮二芳基戊酮类似物的两个苯环的不同位置进行氯化，导致化合物对PMN迁移具有强效抑制作用。 结论 结果表明，这些二芳基戊酮类似物中的一些能够调节吞噬细胞的先天免疫反应的不同步骤，强调它们作为新的免疫调节剂来源的潜力。
• Electrospray ionization tandem mass spectrometry of monoketone curcuminoids
  作者：Tatiana M. Vieira、Renato P. Orenha、Eduardo J. Crevelin、Saulo S.P. Furtado、Ricardo Vessecchi、Renato L.T. Parreira、Antônio E.M. Crotti

  DOI：10.1002/rcm.8699

  日期：2020.9

  reactions of protonated MKCs under collision‐induced dissociation (CID) conditions are still scarce. Here, we combined electrospray ionization tandem mass spectrometry (ESI‐MS/MS) data, multiple‐stage mass spectrometry (MSn), deuterium exchange experiments, accurate‐mass data, and thermochemical data estimated by computational chemistry to elucidate and to rationalize the fragmentation pathways of eleven

  尽管由于其生物活性而对单酮姜黄素（MKC）进行了广泛的研究，但有关碰撞诱导解离（CID）条件下质子化MKC气相裂解反应的数据仍然很少。在这里，我们结合了电喷雾电离串联质谱（ESI-MS / MS）数据，多级质谱（MS n），氘交换实验，精确质量数据和通过计算化学估算的热化学数据，以阐明和合理化11个合成MKC的片段化途径。
• Synthesis and photophysical studies on triazole bridged dendrimers with phenothiazine as a surface unit
  作者：Perumal Rajakumar、Chinnadurai Satheeshkumar、Mahalingam Ravivarma

  DOI：10.3998/ark.5550190.p008.375

  日期：——

  Synthesis and photophysical properties of some novel 1, 2, 3-triazole bridged phenothiazine dendrimers with enone and S-(-)-BINOL core is described.

  描述了一些具有烯酮和 S-(-)-BINOL 核的新型 1, 2, 3-三唑桥接吩噻嗪树枝状聚合物的合成和光物理性质。
• Mesophase behavior and DFT conformational analysis of new symmetrical diester chalcone liquid crystals
  作者：M. Hagar、H.A. Ahmed、T.H. El-Sayed、R. Alnoman

  DOI：10.1016/j.molliq.2019.04.083

  日期：2019.7

  Synthesis, geometrical structures, conformational analysis, mesomorphic and optical characterizations of new angular chalcone liquid crystals, 4-(1,5-(3-oxopenta-1,4-dienyl))diphenyl bis-4-alkoxybenzoates, were investigated. These compounds contain chalcone core and diester phenyl rings attached to symmetrical terminal alkoxy chains with different number (n) of carbons from 6 to 16. Mesomorphic and

  研究了新型角查尔酮液晶4-（1,5-（3-oxopenta-1,4-dienyl））二苯基双-4-烷氧基苯甲酸酯的合成，几何结构，构象分析，同构和光学表征。这些化合物包含查尔酮核和二酯苯环，它们连接到具有6至16个不同碳数（n）的对称末端烷氧基链上。通过差示扫描量热法（DSC）和偏振光学显微镜研究了制备的同系物的同构和光学性质。 POM）。元素分析，FT-IR，1 H和13使用13 C NMR光谱进行分子结构确认。估计了密度泛函理论（DFT）的理论计算量，以确认实验数据并推断出所制备化合物的最稳定的确证方法。结果表明，构象异构体的稳定性和中间相的类型取决于末端烷氧基链的长度。讨论了所有估计构象异构体的热参数，偶极矩和极化率。说明了这些参数的值与构象异构体类型以及中间相稳定性之间的关系。
• Bent shaped H-bonded mesogens derived from 1, 5-bis (4-hydroxyphenyl) penta-1, 4-dien-3-one: Synthesis, photophysical, mesomorphism and computational studies
  作者：Manoj Kr. Paul、Popita Paul、Sandip Kumar Saha、Sudip Choudhury

  DOI：10.1016/j.molliq.2014.05.007

  日期：2014.9

  different linking groups (viz., imine (CHN), azo (NN), ester (COO)) as side wing. The transition temperatures and phase characterization have been investigated by differential scanning calorimetry and polarized optical microscopy. The bent core unit is fluorescent and non-mesogenic, whereas, all the nitrile terminated polar ligands are non-fluorescent and displayed enantiotropic smectic A phase. The H-bonded

  报道了衍生自1、5-双（4-羟苯基）penta-1、4-dien-3-one的新型氢键（H键）弯曲形状的介晶的合成，表征，光物理和同构。H键合弯曲形状的介晶是由1、2摩尔比的1、5-双（4-羟苯基）penta-1、4-dien-3-one作为弯曲单元和极性腈基封端的配体以1：2摩尔比络合形成的连接基团（即亚胺（CH N ），偶氮（N N ），酯（COO））作为侧翼。已经通过差示扫描量热法和偏振光学显微镜研究了转变温度和相表征。弯曲的核单元是荧光的和非介晶的，而所有腈基封端的极性配体都是非荧光的，并表现出对映性近晶A相。氢键复合物是荧光的和介晶的。向列相在两个氢键复合物中被诱导，而其中一个氢键复合物中显示出未知的B x相。进行计算研究以获得化合物的最佳稳定分子结构，研究其电子跃迁并与实验结果进行比较。