(2E,2′E)-1,1′-(1,4-phenylene)bis(3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one)

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2E,2′E)-1,1′-(1,4-phenylene)bis(3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one)
• 英文别名: (E)-1-{4-[(E)-3-(4-hydroxy-3-methoxyphenyl)acryloyl]phenyl}-3-(4-hydroxy-3-methoxyphenyl)-2-propenone；(2E,2'E)-1,1'-(1,4-phenylene)bis(3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one)；1,4-bis-(4-hydroxy-3-methoxy-trans-cinnamoyl)-benzene；1,4-bis-(4-hydroxy-3-methoxy-cinnamoyl)-benzene；1,4-Bis-(4-hydroxy-3-methoxy-trans-cinnamoyl)-benzol；1,4-Bis-(4-hydroxy-3-methoxy-cinnamoyl)-benzol；(E)-3-(4-hydroxy-3-methoxyphenyl)-1-[4-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]phenyl]prop-2-en-1-one
• 化学式: C₂₆H₂₂O₆
• 分子量: 430.457
• InChiKey: URGOMZLQRSOUEU-HMMKTVFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2E,2′E)-1,1′-(1,4-phenylene)bis(3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one) 、 溴 、 溶剂黄146 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Finger; Schott, Journal fur praktische Chemie (Leipzig 1954), 1927, vol. <2> 115, p. 287

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-二乙酰苯 、 香草醛 以 乙醇 为溶剂， 以68.8%的产率得到(2E,2′E)-1,1′-(1,4-phenylene)bis(3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one)
  参考文献：
  名称：

  通过 ROS 和 ER 应激介导的细胞凋亡和细胞焦亡提高抗肺癌稳定性的二羰基姜黄素类似物的合理设计、合成和药理学表征

  摘要：

  摘要 姜黄素是一种具有广泛抗肿瘤活性的天然药物。然而，由于β-二酮部分，姜黄素表现出较差的稳定性和药代动力学，极大地限制了其临床应用。在本文中，通过密度泛函理论计算分子稳定性，设计了两种稳定性得到改善的二羰基姜黄素类似物。合成了二十种化合物，并筛选了它们的抗肿瘤活性。多种类似物的活性明显强于姜黄素。特别是化合物 B2 ((2E,2'E)-3,3'-(1,4-phenylene)bis(1-(2-chlorophenyl)prop-2-en-1-one)) 表现出优异的抗体内和体外肺癌活性. 此外，B2可以上调肺癌细胞中活性氧的水平，进而激活内质网应激，导致细胞凋亡和细胞焦亡。总之，姜黄素类似物 B2 有望成为肺癌治疗的新候选药物，具有改善的化学和生物学特性。

  DOI：

  10.1080/14756366.2022.2116015

文献信息

• Practical Synthesis of Chalcone Derivatives and Their Biological Activities
  作者：Jae-Chul Jung、Yongnam Lee、Dongguk Min、Mankil Jung、Seikwan Oh

  DOI：10.3390/molecules22111872

  日期：——

  especially compound 8 showed very potent anti-inflammatory activity with 1 µM. In addition, the di- and tri-acetylbenzyl derivatives 6, 7, and 8 showed enhanced anti-neurotoxicity activity in cultured cortical neurons. Molecular modelling studies to investigate the chemical structural characteristics required for the enhanced biological activities interestingly revealed that compound 8 has the smallest

  描述了4-羟基-3-甲氧基-2-丙烯衍生物的实用合成和生物活性。通过1，3-或1，4-二乙酰基苯和1，3，5-三乙酰基苯与4-羟基-3-甲氧基苯甲醛的酸催化一步缩合反应制备新型查耳酮衍生物。然后评估它们的自由基清除活性，抑制脂多糖（LPS）诱导的NO生成和体外抗兴奋性毒性。发现所有化合物均对清除2，2-二苯基-1-吡啶并肼基（DPPH），清除LPS诱导的NO生成和抗神经毒性具有良好的作用。化合物6和7在浓度范围为10 µM时是有效的NO生成抑制剂，尤其是化合物8在1 µM时显示出非常有效的抗炎活性。另外，二和三乙酰基苄基衍生物6、7 图8和8显示了在培养的皮层神经元中增强的抗神经毒性活性。分子模型研究对增强生物活性所需的化学结构特征进行了研究，有趣的是，化合物8具有最小的最高占据分子轨道-最低能量的未占据分子轨道（HOMO-LUMO）间隙，这表明HOMO和H2O之间易于进行电子和自由基转移。
• Symmetric Bis-chalcones as a New Type of Breast Cancer Resistance Protein Inhibitors with a Mechanism Different from That of Chromones
  作者：Evelyn Winter、Patrícia Devantier Neuenfeldt、Louise Domeneghini Chiaradia-Delatorre、Charlotte Gauthier、Rosendo Augusto Yunes、Ricardo José Nunes、Tânia Beatriz Creczynski-Pasa、Attilio Di Pietro

  DOI：10.1021/jm401879z

  日期：2014.4.10

  Potent ABCG2 inhibitors were recently identified as asymmetric chromones with different types of substituents. We here synthesized symmetric bis-chalcones that were differently substituted and screened for their ability to inhibit mitoxantrone efflux from ABCG2-transfected HEK293 cells. Potent bis-chalcone inhibitors were identified, the efficiency depending on both position of the central ketone groups and the number and positions of lateral methoxy substituents. The best derivative, namely, 1p, was selective for ABCG2 over P-glycoprotein and MRP1, appeared not to be transported by ABCG2, and was at least as active on various drug-selected cancer cells overexpressing ABCG2. Compound 1p stimulated the ABCG2 basal ATPase activity by contrast to a chromone lead that inhibited it, suggesting different mechanisms of interaction. Combination of both types of inhibitors produced synergistic effects, leading to complete inhibition at very low
• Lampe; Taczanowska, Roczniki Chemii, 1934, vol. 14, p. 1226,1228
  作者：Lampe、Taczanowska

  DOI：——

  日期：——
• Reversible Thermochromic Compositions
  申请人：Rossi Mirko

  公开号：US20100234522A1

  公开（公告）日：2010-09-16

  The present invention pertains to a reversible thermochromic system comprising a β-phenylvinylketone or a ω-phenyl polyacetylenyl ketone with at least one acidic hydrogen and a base and to a reversible thermochromic composition comprising the reversible thermochromic system and a carrier material and to novel substituted β-phenylvinylketones or ω-phenyl polyacetylenyl ketones with at least one acidic hydrogen.
• US8273822B2
  申请人：——

  公开号：US8273822B2

  公开（公告）日：2012-09-25