7-(diethylamino)-3-(1-phenyl-1H-benzo[d]imidazol-2-yl)-2H-chromen-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 7-(diethylamino)-3-(1-phenyl-1H-benzo[d]imidazol-2-yl)-2H-chromen-2-one
• 英文别名: 3-(1-phenyl-1H-benzo[d]imidazole-2-yl)-7-(diethylamino)coumarin；7-(diethylamino)-3-(1-phenyl-1H-benzo[d]imidazol-2-yl)coumarin；7-(Diethylamino)-3-(1-phenylbenzimidazol-2-yl)chromen-2-one
• 化学式: C₂₆H₂₃N₃O₂
• 分子量: 409.488
• InChiKey: AHELLSFQAMDSIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-(二乙胺基)香豆素-3-甲酸乙酯 在 水 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 7-(diethylamino)-3-(1-phenyl-1H-benzo[d]imidazol-2-yl)-2H-chromen-2-one
  参考文献：
  名称：

  Design, Synthesis, andIn VitroEvaluation of Novel 3, 7-Disubstituted Coumarin Derivatives as Potent Anticancer Agents

  摘要：

  Twenty‐seven 3, 7‐disubstituted coumarin derivatives were designed, synthesized, and evaluated in vitro as anticancer agents. Most of the compounds showed moderate‐to‐potent antiproliferative activity against K562 cells. Compounds 7b and 7d were chosen to evaluate the concentration of 50% growth inhibition (GI50) against SN12C, OVCAR, BxPC‐3, KATO‐III, T24, SNU‐1, WiDr, HeLa, K562, and AGS cell lines. The most potent compound 7d was selected for further cell cycle arrest assay in the AGS cell line. The in vitro data indicated that methylation of benzimidazole moiety at the 3‐position of coumarin exhibited significant enhancement of anticancer activity. This study should provide important information for further modification and optimization of coumarin derivatives as anticancer agents.

  DOI：

  10.1111/cbdd.12531

文献信息

• Synthesis and fluorescent properties of coumarin-benzimidazole and coumarin–phenanthroimidazole hybrids
  作者：Hongli Fan、Lingqiang Wang、Xiaolong Wang

  DOI：10.1177/1747519819882229

  日期：2020.1

  Two coumarin-benzimidazole hybrids and two coumarin-phenanthroimidazole conjugates were conveniently synthesized and characterized. The UV–vis absorption, emission spectra, absolute quantum yields, and fluorescence lifetimes of these compounds in diluted dichloromethane solutions were measured.

  两种香豆素-苯并咪唑杂化物和两种香豆素-菲咪唑缀合物被方便地合成和表征。测量了这些化合物在稀释的二氯甲烷溶液中的 UV-vis 吸收、发射光谱、绝对量子产率和荧光寿命。
• Functionalized coumarin derivatives containing aromatic-imidazole unit as organic luminescent materials
  作者：Youjia Wang、Yanmei Li、Tianzhi Yu、Wenming Su、Hailin Ma、Yuling Zhao、Xinyu Li、Hui Zhang

  DOI：10.1016/j.dyepig.2019.107958

  日期：2020.2

  new coumarin derivatives containing aromatic-imidazole unit (i.e., benzo[d]imidazole, phenanthro[9,10-d]imidazole and pyreno[4,5-d]imidazole), 3-(1-phenyl-1H-benzo[d]imidazole-2-yl)-7-(diethylamino)coumarin (BI–C), 3-(1-(4-(tert-butyl)phenyl)-1H-phenanthro[9,10-d]imidazole-2-yl)-7-(diethylamino)coumarin (PI–C) and 3-(9-(4-(tert-butyl)phenyl)-9H-pyreno[4,5-d]imidazole-10-yl)-7-(diethylamino)coumarin (PyI-C)

  三种含有芳族咪唑单元的新香豆素衍生物（即苯并[ d ]咪唑，菲[ 9,10- d ]咪唑和吡啶并[4,5- d ]咪唑），3-（1-苯基-1 H-苯并[ d ]咪唑-2-基）-7-（二乙氨基）香豆素（BI–C），3-（1-（4-（叔丁基）苯基）-1 H-菲基[9,10- d ]咪唑-2-基）-7-（二乙氨基）香豆素（PI–C）和3-（9-（4-（叔丁基）苯基）-9 H-吡喃并[4,5- d ]咪唑-10-基）-7-（二乙氨基）香豆素（PyI-C），已成功地准备好用于有机发光器件。这些化合物由于刚性多芳族咪唑骨架的π共轭扩展而显示出良好的热性能和从蓝绿色到绿色的强烈发射，并且在氯仿溶液中具有94％，97％和98％的高光致发光量子效率。在这些化合物中，由化合物PI-C制成的掺杂的有机发光器件表现出6.07cd / A的最大发光效率和2.78％的最大EQE。