(E)-3-(3,4-dimethoxyphenyl)-1-(4-((6,7-dimethoxyquinazolin-4-yl)amino)phenyl) 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: (E)-3-(3,4-dimethoxyphenyl)-1-(4-((6,7-dimethoxyquinazolin-4-yl)amino)phenyl) prop-2-en-1-one
• 英文别名: (E)-3-(3,4-dimethoxyphenyl)-1-[4-[(6,7-dimethoxyquinazolin-4-yl)amino]phenyl]prop-2-en-1-one
• 化学式: C₂₇H₂₅N₃O₅
• 分子量: 471.513
• InChiKey: PDKMJUAYGJBRSL-VZUCSPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  91.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-氯-6,7-二甲氧基喹唑啉 在 sodium hydroxide 作用下， 以 乙醇 、 水 、 异丙醇 为溶剂， 反应 5.0h， 生成 (E)-3-(3,4-dimethoxyphenyl)-1-(4-((6,7-dimethoxyquinazolin-4-yl)amino)phenyl) prop-2-en-1-one
  参考文献：
  名称：

  喹唑啉查尔酮衍生物的新型杂种分子：体外细胞毒性活性的合成和研究

  摘要：

  背景：合成了一系列新的喹唑啉连接查尔酮缀合物，并对其体外细胞毒性进行了评估。 方法：喹唑啉-查尔酮衍生物（13a-r）是通过各种取代的苯甲醛（12a-r）与取代的1-（4-（3，4-二氢喹唑啉-4-基氨基）苯基）的克莱森-施密特缩合反应制得的NaOH水溶液中的乙酮（11a-b）。三种潜在的化合物13f，13g和13h对白血病表现出细胞毒性（GI50值为1.07、0.26和0.24 µM），非小肺（GI50值为2.05、1.32和0.23 µM），结肠（GI50值为0.54、0.34和0.34） µM）和乳腺癌（GI50值分别为2.17、1.84和0.22 µM）细胞系。 结果与结论：基于这些生物学结果，很明显，化合物13h有可能被单独或与作为潜在抗癌药的现有疗法组合进行进一步详细研究。

  DOI：

  10.2174/1570180814666171013162148

文献信息

• The combination of quinazoline and chalcone moieties leads to novel potent heterodimeric modulators of breast cancer resistance protein (BCRP/ABCG2)
  作者：Stefanie Kraege、Katja Stefan、Kapil Juvale、Thomas Ross、Thomas Willmes、Michael Wiese

  DOI：10.1016/j.ejmech.2016.03.067

  日期：2016.7

  During the last decade it has been found that chalcones and quinazolines are promising inhibitors of ABCG2. The combination of these two scaffolds offers a new class of heterocyclic compounds with potentially high inhibitory activity against ABCG2. For this purpose we investigated 22 different heterodimeric derivatives. In this series only methoxy groups were used as substituents as these had been proven superior for inhibitory activity of chalcones. All compounds were tested for their inhibitory activity, specificity and cytotoxicity. The most potent ABCG2 inhibitor in this series showed an IC50 value of 0.19 mu M. It possesses low cytotoxicity (GI(50) = 93 mu M), the ability to reverse MDR and is nearly selective toward ABCG2. Most compounds containing dimethoxy groups showed slight activity against ABCB1 too. Among these three compounds (17,19 and 24) showed even higher activity toward ABCB1 than ABCG2. All inhibitors were further screened for their effect on basal ATPase activity. Although the basal ATPase activity was partially stimulated, the compounds were not transported by ABCG2. Thus, quinazoline-chalcones are a new class of effective ABCG2 inhibitors. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Novel Hybrid Molecules of Quinazoline Chalcone Derivatives: Synthesis and Study of in vitro Cytotoxic Activities
  作者：Arunkumar Thiriveedhi、Ratnakaram Venkata Nadh、Navuluri Srinivasu、Kishore Kaushal

  DOI：10.2174/1570180814666171013162148

  日期：2018.5.30

  Background: A new series of quinazoline linked chalcone conjugates were synthesized and evaluated for their in vitro cytotoxicity. Methods: The quinazoline-chalcone derivatives (13a-r) have been prepared by the Claisen-Schmidt condensation of various substituted benzaldehydes (12a-r) with substituted l-(4-(3,4- dihydroquinazolin-4-ylamino)phenyl)ethanone (11a-b) in the presence of aqueous NaOH. Three

  背景：合成了一系列新的喹唑啉连接查尔酮缀合物，并对其体外细胞毒性进行了评估。 方法：喹唑啉-查尔酮衍生物（13a-r）是通过各种取代的苯甲醛（12a-r）与取代的1-（4-（3，4-二氢喹唑啉-4-基氨基）苯基）的克莱森-施密特缩合反应制得的NaOH水溶液中的乙酮（11a-b）。三种潜在的化合物13f，13g和13h对白血病表现出细胞毒性（GI50值为1.07、0.26和0.24 µM），非小肺（GI50值为2.05、1.32和0.23 µM），结肠（GI50值为0.54、0.34和0.34） µM）和乳腺癌（GI50值分别为2.17、1.84和0.22 µM）细胞系。 结果与结论：基于这些生物学结果，很明显，化合物13h有可能被单独或与作为潜在抗癌药的现有疗法组合进行进一步详细研究。