N-(4-(2-oxo-4-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-2H-chromen-3-yl)phenyl)acetamide | 1613152-66-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: N-(4-(2-oxo-4-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-2H-chromen-3-yl)phenyl)acetamide
• CAS: 1613152-66-1
• 化学式: C₃₀H₃₀N₂O₄
• 分子量: 482.579
• InChiKey: HCACXWUOLDCJAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  71.78
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(4-(2-oxo-4-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-2H-chromen-3-yl)phenyl)acetamide 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以98%的产率得到3-(4-aminophenyl)-4-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-2H-chromen-2-one
  参考文献：
  名称：

  Cytotoxicity and DNA binding property of the dimers of triphenylethylene–coumarin hybrid with one amino side chain

  摘要：

  Novel dimers of triphenylethylene-coumarin hybrid containing one amino side chain were designed and synthesized by the condensation of four dicarboxylic acids with the amino monomeric hybrids catalyzed by HATU and DIPEA at room temperature. The adding order of the reactants had a significant effect on the condensation reaction when the malonic acid was used. The dimeric compounds 7a and 7b linked by the malonic acid, showed a broad-spectrum and good anti-proliferative activity against four tumor cells and low cytotoxicity in osteoblast. UV-vis, fluorescence, and circular dichroism (CD) spectroscopies and thermal denaturation exhibited that compounds 7b, 8b, 9b, and 10b had significant interactions with Ct-DNA by the intercalative mode of binding. Both the DNA binding properties and the anti-proliferative activities would be enhanced by dimerization of the monomeric hybrid with one amino side chain, and were significantly affected by the length of the linker (dicarboxylic acids). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.106
• 作为产物：
  描述：

  (2-羟基苯基)-(4-甲氧基苯基)甲酮 在 三溴化硼 、 potassium carbonate 、 silver nitrate 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 1.25h， 生成 N-(4-(2-oxo-4-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-2H-chromen-3-yl)phenyl)acetamide
  参考文献：
  名称：

  Cytotoxicity and DNA binding property of the dimers of triphenylethylene–coumarin hybrid with one amino side chain

  摘要：

  Novel dimers of triphenylethylene-coumarin hybrid containing one amino side chain were designed and synthesized by the condensation of four dicarboxylic acids with the amino monomeric hybrids catalyzed by HATU and DIPEA at room temperature. The adding order of the reactants had a significant effect on the condensation reaction when the malonic acid was used. The dimeric compounds 7a and 7b linked by the malonic acid, showed a broad-spectrum and good anti-proliferative activity against four tumor cells and low cytotoxicity in osteoblast. UV-vis, fluorescence, and circular dichroism (CD) spectroscopies and thermal denaturation exhibited that compounds 7b, 8b, 9b, and 10b had significant interactions with Ct-DNA by the intercalative mode of binding. Both the DNA binding properties and the anti-proliferative activities would be enhanced by dimerization of the monomeric hybrid with one amino side chain, and were significantly affected by the length of the linker (dicarboxylic acids). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.106