feruloylacetone | 1924-25-0

• 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
• 英文名称: feruloylacetone
• 英文别名: 6-(4-Hydroxy-3-methoxyphenyl)hex-5-ene-2,4-dione
• CAS: 1924-25-0
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: SQDOMQCCCHMXBP-UHFFFAOYSA-N

物化性质

• 熔点：
  146-147 °C
• 沸点：
  403.9±40.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  feruloylacetone 在 吡啶 、 aluminum (III) chloride 、 盐酸 作用下， 以 乙酸乙酯 、 水 为溶剂， 反应 7.25h， 以51%的产率得到demethoxy-feruloylacetone
  参考文献：
  名称：

  Bisdemethylcurcumin and structurally related hispolon analogues of curcumin exhibit enhanced prooxidant, anti-proliferative and anti-inflammatory activities in vitro

  摘要：

  Curcumin, a component of turmeric (Curcuma longa), exhibits anti-inflammatory and anti-proliferative activities through the generation of reactive oxygen species (ROS). Curcumin (diferuloylmethane) contains two hydroxyl, two methoxy and two phenyl groups but how these groups contribute to its activity is poorly understood. We synthesized analogues that varied in inclusion of these groups and compared their activity. We found that bisdemethylcurcumin (BDC) was more potent than curcumin as an anti-inflammatory agent as indicated by suppression of TNF-induced NF-kappa B activation, more potent as an anti-proliferative agent, and more potent in inducing ROS. Hispolon, which lacks one aromatic unit in relation to curcumin, also exhibited enhanced anti-inflammatory and anti-proliferative activities. When synthetic curcumin (Cur-S) was compared with bisdemethylcurcumin (BDC), hispolon, hispolon methyl ether (HME), dehydroxy hispolon (DH), hydroxy hispolon (HH), methoxy hispolon methyl ether (MHME), and methoxy hispolon (MH), we found that following order of anti-inflammatory activity: BDC = Hispolon > HME > HH > Cur-S> MHME > MH > DH; for anti-proliferative: Hispolon > BDC > MHME > Cur-S > MR > HME = HH > DH; and for prooxidant: BDC > CurS = MHME > FIR > MR + HME > DH (254-1414 mean fluorescence intensity). Thus, dehydroxy hispolon was least potent for all three activities. Overall the results indicate that the substitution of a hydroxyl group for a methoxy group at the meta positions of the phenyl rings in curcumin significantly enhanced the anti-inflammatory activity, and the removal of phenyl ring at the 7(th) position of the heptadiene back bone and addition of hydroxyl group significantly increased the anti-proliferative activity of curcumin. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2010.01.033
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 alkali 作用下， 生成 feruloylacetone
  参考文献：
  名称：

  Lampe, Chemische Berichte, 1918, vol. 51, p. 1351

  摘要：

  DOI：

文献信息

• NOVEL CURCUMIN DERIVATIVE
  申请人：Sugimoto Hachiro

  公开号：US20110082295A1

  公开（公告）日：2011-04-07

  To develop a highly safe measure to treat Alzheimer's disease using a secretase-inhibiting substance, there is provided a compound represented by the following general formula (I) or a salt thereof: wherein A represents a phenyl group or the like, R 1 represents a chlorine atom, a bromine atom, or a nitro group or the like, R 2 , R 3 , R 4 , and R 5 each represent a hydrogen atom or the like, and L represents CH 2 —CH 2 or CH═CH.

  为了开发一种高度安全的措施来治疗阿尔茨海默病，提供了一种由以下一般式（I）或其盐表示的化合物： 其中A代表苯基或类似物，R1代表氯原子、溴原子或硝基团等，R2、R3、R4和R5各自代表氢原子或类似物，L代表CH2— 或CH═CH。
• Lys修饰的姜黄素衍生物、其合成及应用
  申请人：首都医科大学

  公开号：CN104610089B

  公开（公告）日：2017-02-01

  本发明公开了下式的伪肽，进一步公开了它们的制备方法和用途。本发明的伪肽具有优秀的溶血栓活性、抗血栓活性、抗炎活性、OH自由基清除活性以及纳米结构。
• Development of curcumin-based amyloid β aggregation inhibitors for Alzheimer's disease using the SAR matrix approach
  作者：Rohmad Yudi Utomo、Yasunobu Asawa、Satoshi Okada、Hyun Seung Ban、Atsushi Yoshimori、Jürgen Bajorath、Hiroyuki Nakamura

  DOI：10.1016/j.bmc.2021.116357

  日期：2021.9

  Amyloid β (Aβ) aggregation inhibitor activity cliff involving a curcumin structure was predicted using the SAR Matrix method on the basis of 697 known Aβ inhibitors from ChEMBL (data set 2487). Among the compounds predicted, compound B was found to possess approximately 100 times higher inhibitory activity toward Aβ aggregation than curcumin. TEM images indicate that compound B induced the shortening

  基于来自 ChEMBL 的 697 种已知 Aβ 抑制剂（数据集 2487），使用 SAR 矩阵方法预测了涉及姜黄素结构的淀粉样蛋白 β (Aβ) 聚集抑制剂活性悬崖。在预测的化合物中，发现化合物B对 Aβ 聚集的抑制活性比姜黄素高约 100 倍。TEM 图像表明化合物B以浓度依赖性方式诱导 Aβ 原纤维缩短并增加 Aβ 寡聚体的产生。此外，化合物K，其中化合物B的甲酯被叔丁酯取代，对N2A细胞具有低细胞毒性并减弱Aβ诱导的细胞毒性，表明化合物K 将具有预防由 Aβ 聚集引起的神经毒性的能力。
• 一种线粒体靶向的姜黄素衍生物及其制备方法与医药用途
  申请人：蔡世忠

  公开号：CN113135956A

  公开（公告）日：2021-07-20

  本发明涉及天然药物及药物化学领域，具体涉及一类靶向线粒体的姜黄素衍生物。本发明还公开了这些姜黄素衍生物的制备方法以及其在靶向线粒体来发挥抗肿瘤功效方面的应用。
• Synthesis, screening and docking analysis of hispolon analogs as potential antitubercular agents
  作者：Neduri V. Balaji、Bollikolla Hari Babu、Gottumukkala V. Subbaraju、Kurre Purna Nagasree、Muthyala Murali Krishna Kumar

  DOI：10.1016/j.bmcl.2016.11.047

  日期：2017.1

  series of 20 hispolons/dihydrohispolons were synthesized and characterized by spectral data. These compounds were subjected to in vitro antitubercular activity screening against Mycobacterium tuberculosis (H37Rv) strain. The synthesized compounds showed varied antitubercular activity ranging from 100 to 1.6μg/mL. Among the screened compounds, four compounds (H1, H2, H3 and H15) have shown moderate activity

  合成了一系列的20个Hispolons / dihydrohispolons，并通过光谱数据对其进行了表征。对这些化合物进行了针对结核分枝杆菌（H37Rv）菌株的体外抗结核活性筛选。合成的化合物显示出从100到1.6μg/ mL的变化的抗结核活性。在筛选出的化合物中，四种化合物（H1，H2，H3和H15）具有中等活性，MIC为25μg/ mL。观察到二氢hispolon衍生物H14（MIC1.6μg/ mL），然后是H13（6.25μg/ mL）和H17（12.5μg/ mL），H19（3.125μg/ ML）的活性。对接模拟对测试化合物与β-酮酰基合酶（mtbFabH）之间可能的相互作用提供了很好的见解。药物-抑制剂组合研究显示，与针对霉菌酸生物合成的药物没有协同作用（异烟肼，