(E)-3-(4-methoxyphenyl)-1-(4-((2-phenylquinazolin-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-(4-methoxyphenyl)-1-(4-((2-phenylquinazolin-4-yl)amino)phenyl)prop-2-en-1-one
• 英文别名: (E)-3-(4-methoxyphenyl)-1-[4-[(2-phenylquinazolin-4-yl)amino]phenyl]prop-2-en-1-one
• 化学式: C₃₀H₂₃N₃O₂
• 分子量: 457.532
• InChiKey: BSRICBDZFIHXJC-DEDYPNTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-methoxyphenyl)-1-(4-((2-phenylquinazolin-4-yl)amino)phenyl)prop-2-en-1-one 生成 4--2-phenylquinazoline
  参考文献：
  名称：

  MAHMOUD, A. M.;EL-SHERIEF, H. A. H.;ESMAIEL, A. A., ACTA CHIM. HUNG., 1983, 113, N 3, 247-256

  摘要：

  DOI：
• 作为产物：
  描述：

  2-苯基-4-[3H]喹唑啉酮 在 lithium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 9.5h， 生成 (E)-3-(4-methoxyphenyl)-1-(4-((2-phenylquinazolin-4-yl)amino)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  The combination of quinazoline and chalcone moieties leads to novel potent heterodimeric modulators of breast cancer resistance protein (BCRP/ABCG2)

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2016.03.067