(2E,2′E)-3,3′-(1,4-phenylene)bis(1-(3,5-dimethoxyphenyl)prop-2-en-1-one) | 1584741-42-3

• 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)-3,3′-(1,4-phenylene)bis(1-(3,5-dimethoxyphenyl)prop-2-en-1-one)
• 英文别名: (2E,2'E)-3,3'-(1,4-phenylene)bis(1-(3,5-dimethoxyphenyl)prop-2-en-1-one)；(E)-1-(3,5-dimethoxyphenyl)-3-[4-[(E)-3-(3,5-dimethoxyphenyl)-3-oxoprop-1-enyl]phenyl]prop-2-en-1-one
• CAS: 1584741-42-3
• 化学式: C₂₈H₂₆O₆
• 分子量: 458.511
• InChiKey: SPXDXQMUVSMXCX-WGDLNXRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,5-二甲氧基苯乙酮 、 对苯二甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以56.9%的产率得到(2E,2′E)-3,3′-(1,4-phenylene)bis(1-(3,5-dimethoxyphenyl)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

• 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