2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone | 7249-34-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone
• 英文别名: 2,5-Vanillyliden-cyclopentanon；2,5-divanillylidene-cyclopentanone；2,5-Divanillyliden-cyclopentanon；2,5-Bis[(4-hydroxy-3-methoxyphenyl)methylidene]-1-cyclopentanone；2,5-bis[(4-hydroxy-3-methoxyphenyl)methylidene]cyclopentan-1-one
• CAS: 7249-34-5
• 化学式: C₂₁H₂₀O₅
• mdl: MFCD00601691
• 分子量: 352.387
• InChiKey: NZSRSKNDCCSSGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone 在 1,4-二氧六环 、 铂 作用下， 生成 2,5-divanillyl-cyclopentanone
  参考文献：
  名称：

  Cyclopentanone compound

  摘要：

  公开号：

  US02803660A1
• 作为产物：
  描述：

  3-甲氧基-4-[(四氢-2H-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 2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone
  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

• Solvent-free catalytic preparation of 2,6-dibenzylidenecycloalkanones using 2-hydroxyethylammonium acetate ionic liquid as catalyst
  作者：Li Q. Kang、Yue Q. Cai、Hao Wang、Li H. Li

  DOI：10.1007/s00706-013-1082-8

  日期：2014.2

  AbstractVarious 2,6-dibenzylidenecycloalkanones were readily prepared in a condensation reaction catalyzed by 2-hydroxyethylammonium acetate ionic liquid under solvent-free conditions in excellent yields. The major advantages of the present method are high yields, short reaction times, lack of solvent, simplicity of performance, and low cost. Graphical abstract

  摘要在无溶剂条件下，由乙酸2-羟乙基铵离子液体催化的缩合反应中，很容易制得各种2,6-二亚苄基环烷酮。本方法的主要优点是产率高，反应时间短，溶剂少，性能简单和成本低。 图形概要
• Diarylidenecyclopentanone derivatives as potent anti-inflammatory and anticancer agents
  作者：Nitesh Tamang、Gayathri Ramamoorthy、Mayank Joshi、Angshuman Roy Choudury、Siva Kumar B.、Nageswara Rao Golakoti、Mukesh Doble

  DOI：10.1007/s00044-020-02578-5

  日期：2020.9

  Cancer is often associated with chronic inflammation. In order to develop potential anticancer and anti-inflammatory agents a series of 26 diarylidenecyclopentanones (DACPs) Ia–Iv, II, III, and IV were synthesized. Five of the synthesized DACPs are novel (Ih, Ij, Ik, Is, and Iv), derivative Iv was characterized using single-crystal X-ray diffraction study. All the synthesized derivatives were tested

  癌症通常与慢性炎症有关。为了开发潜在的抗癌药和抗炎药，合成了26种二芳基亚环戊酮（DACP）Ia-Iv，II，III和IV。合成的DACP中有五个是新颖的（Ih，Ij，Ik，Is和Iv），使用单晶X射线衍射研究表征了衍生物Iv。测试所有合成的衍生物的抗炎和细胞毒性。复合是通过抑制PGE 2（前列腺素E 2）的产生，发现其具有最高的抗炎活性（93.67％）。观察到三个DACP s（Io，It和Iu）具有很高的细胞毒性，对HeLa的IC 50值分别为8.73±0.06 µM（Io），12.55±0.31 µM（It）和11.47±0.15 µM（Iu）细胞。使用这三个DACP进行了进一步的染色和细胞周期分析，以了解其作用机理。观察到G 0 / G 1相是细胞经历凋亡的最长相。
• Vanillin-derived epoxy monomer for synthesis of bio-based epoxy thermosets: effect of functionality on thermal, mechanical, chemical and structural properties
  作者：Mohsen Mogheiseh、Ramin Karimian、Mostafa Khoshsefat

  DOI：10.1007/s11696-020-01164-8

  日期：2020.10

  Tri-functional vanillin-derived epoxy monomer was developed through the synthesized di-functional reagent and cured with a series of different types of hardeners (hydroxyl and amine based) to evaluate thermo-mechanical properties of the resultant epoxy thermosets. Through elevating of curing degree by the hardeners, both alpha transition temperature (Tα) and cross-linking density (υ) slightly increased (up to 118 °C and 69.9 mol m−3). However, the highest values of storage and loss modulus (E′ and E″, respectively) were obtained using trimethylolpropane (TMP) in epoxy thermoset systems cooperating with tri-functional epoxy monomer at 3200 MPa and 359.3 MPa, respectively. The sample produced by TMP exhibited the highest amount of statistic heat-resistant index (Ts) (up to 193 °C). Nevertheless, the longest half-life and the highest Td are obtained for the sample prepared by incorporation of tris(hydroxymethyl)aminomethane (TRIS) and 1,10-diaminodecane (1347 s, 431 °C, respectively) containing amine agents as curing agent. Remarkably, the sample comprising triethanol amine showed the highest char yield (3.3 mg at 700 °C) among the all samples. However, the sample cured by TRIS exhibited the highest elasticity, elongation and tensile strength among the obtained samples (up to 0.48 GPa, 6.56% and 22.90 MPa, respectively).

  通过合成的二官能试剂开发了三官能香兰素衍生环氧单体，并用一系列不同类型的固化剂（羟基和胺基）进行固化，以评估所得环氧热固性塑料的热机械性能。通过提高固化剂的固化度，α转变温度（Tα）和交联密度（υ）都略有增加（分别高达 118 ℃ 和 69.9 mol m-3）。然而，在环氧热固性体系中使用三羟甲基丙烷（TMP）与三官能团环氧单体合作，获得了最高的储存模量和损耗模量（E′和 E″）值，分别为 3200 MPa 和 359.3 MPa。由 TMP 制成的样品显示出最高的统计耐热指数（Ts）（高达 193 °C）。然而，加入三（羟甲基）氨基甲烷（TRIS）和 1,10-二氨基癸烷（分别为 1347 s、431 ℃）作为固化剂的样品的半衰期最长，Td 最高。值得注意的是，在所有样品中，含有三乙醇胺的样品显示出最高的炭化率（3.3 mg，700 ℃）。然而，在所获得的样品中，用 TRIS 固化的样品显示出最高的弹性、伸长率和拉伸强度（分别高达 0.48 GPa、6.56% 和 22.90 MPa）。
• Curcumin and a hemi-analogue with improved blood–brain barrier permeability protect against amyloid-beta toxicity in <i>Caenorhabditis elegans</i> via SKN-1/Nrf activation
  作者：Elaine Hui-Chien Lee、Sherlyn Sheau-Chin Lim、Kah-Hay Yuen、Chong-Yew Lee

  DOI：10.1111/jphp.13052

  日期：2019.4.12

  This study aims to investigate the blood–brain barrier (BBB) permeability of curcumin analogues with shortened linkers and their ability to protect against amyloid-beta toxicity in a whole organism model.

  Four curcumin analogues were synthesized. These analogues and curcumin were evaluated for their BBB permeability in the parallel artificial membrane permeability assay. The transgenic Caenorhabditis elegansGMC101 that expresses human Aβ1–42 was treated with the compounds to evaluate their ability to delay Aβ-induced paralysis. Expression of skn-1mRNA was examined on nematodes treated with selected efficacious compounds. In vitro Aβ aggregation in the presence of the compounds was performed.

  The four analogues showed improved BBB permeability vs curcumin in the PAMPA with the hemi-analogue C4 having the highest permeability coefficient. At 100 μm, analogues C1 and C4 as well as curcumin significantly prolonged the survival of the nematodes protecting against Aβ toxicity. However, only curcumin and C4 showed protection at lower concentrations. skn-1mRNA was significantly elevated in nematodes treated with curcumin and C4 indicating SKN-1/Nrf activation as a possible mode of action.

  Analogue C4 provides a new lead for the development of a curcumin-based compound for protection against Aβ toxicity with an improved BBB permeability.

  本研究旨在调查缩短连接剂的姜黄素类似物对血脑屏障（BBB）的渗透性以及它们在整个生物模型中保护免受淀粉样蛋白β毒性的能力。

  合成了四种姜黄素类似物。在平行人工膜渗透性试验中评估了这些类似物和姜黄素的BBB渗透性。用这些化合物处理表达人类Aβ1-42的转基因秀丽隐杆线虫GMC101，以评估它们延迟Aβ诱导的麻痹能力。检查用有效化合物处理的线虫中skn-1mRNA的表达。在化合物存在下进行了体外Aβ聚集实验。

  四种类似物在PAMPA中显示出比姜黄素更好的BBB渗透性，其中半类似物C4的渗透系数最高。在100微米下，类似物C1和C4以及姜黄素显著延长了线虫的存活时间，保护免受Aβ毒性。然而，只有姜黄素和C4在较低浓度下表现出保护作用。用姜黄素和C4处理的线虫中skn-1mRNA明显升高，表明SKN-1 / Nrf激活可能是一种可能的作用方式。

  类似物C4为开发一种基于姜黄素的化合物，以保护免受Aβ毒性并具有更好BBB渗透性的新线索。

• Synthesis of Renewable High-Density Fuel with Vanillin and Cyclopentanone Derived from Hemicellulose
  作者：Wei Wang、Ling An、Chi Qian、Yanqing Li、Meiping Li、Xianzhao Shao、Xiaohui Ji、Zhizhou Li

  DOI：10.3390/molecules28135029

  日期：——

  catalysis of sulphuric acid. Over the optimized condensation, a high carbon yield (82.6%) of 2,5-bis(4-hydroxy-3-methoxybenzylidene) cyclopentanone was achieved at 80 ºC. In the second step, 2,5-bis(4-hydroxy-3-methoxybenzylidene) cyclopentanone was hydrodeoxygenated over the Pd/HY catalyst in cyclohexane as solvent. High carbon yields of 1,3-bis(cyclohexylmethyl)cyclopentane (96.2%) was obtained. The

  1,3-双（环己基甲基）环戊烷是一种可再生高密度燃料，首先用源自生物质的香草醛和环戊酮以高总碳产率（79.5%）生产。本工作中使用的合成路线包含两个步骤。第一步，香草醛与环戊酮在硫酸催化下进行羟醛缩合，合成2,5-双(4-羟基-3-甲氧基亚苄基)环戊酮。通过优化的缩合，在 80 ℃ 下获得了高碳收率 (82.6%) 的 2,5-双(4-羟基-3-甲氧基亚苄基)环戊酮。第二步，2,5-双(4-羟基-3-甲氧基亚苄基)环戊酮在Pd/HY催化剂上在环己烷溶剂中加氢脱氧。获得高碳收率的1,3-双(环己基甲基)环戊烷(96.2％)。所得多环烷烃混合物的密度为0.943 g mL−1，凝固点为-35 °C。它可以混合到传统的高密度燃料（例如 JP-10）中，用于火箭和导弹推进，作为潜在的应用。