(2E,2′E)-3,3′-(1,4-phenylene)bis(1-(2,5-dimethoxyphenyl)prop-2-en-1-one) | 1584741-41-2

• 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-(2,5-dimethoxyphenyl)prop-2-en-1-one)
• 英文别名: (E)-1-(2,5-dimethoxyphenyl)-3-[4-[(E)-3-(2,5-dimethoxyphenyl)-3-oxoprop-1-enyl]phenyl]prop-2-en-1-one
• CAS: 1584741-41-2
• 化学式: C₂₈H₂₆O₆
• 分子量: 458.511
• InChiKey: NBWAXADCFREQMT-UTLPMFLDSA-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：

  2,5-二甲氧基苯乙酮 、 对苯二甲醛 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以84%的产率得到(2E,2′E)-3,3′-(1,4-phenylene)bis(1-(2,5-dimethoxyphenyl)prop-2-en-1-one)
  参考文献：
  名称：

  Symmetric Bis-chalcones as a New Type of Breast Cancer Resistance Protein Inhibitors with a Mechanism Different from That of Chromones

  摘要：

  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

  DOI：

  10.1021/jm401879z

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