7-(diethylamino)-3-(5-methyl-1H-benzo[d]imidazol-2-yl)-2H-chromen-2-one | 53350-28-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-(diethylamino)-3-(5-methyl-1H-benzo[d]imidazol-2-yl)-2H-chromen-2-one
• 英文别名: 3-(5'-methyl-2'-benzimidazole)-7-diethylamino-2H-1-benzopyran-2-one；7-diethylamino-3-(5-methyl-1H-benzoimidazol-2-yl)-chromen-2-one；7-(diethylamino)-3-(6-methyl-1H-benzimidazol-2-yl)chromen-2-one
• CAS: 53350-28-0
• 化学式: C₂₁H₂₁N₃O₂
• 分子量: 347.417
• InChiKey: QHQXZNBFZVXLIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  610.9±65.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  58.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 溶剂黄146 作用下， 反应 3.0h， 生成 7-(diethylamino)-3-(5-methyl-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

• One-pot catalyst-free synthesis of 3-heterocyclic coumarins
  作者：Shaoliang Jiang、Jianrong Gao、Liang Han

  DOI：10.1007/s11164-015-2070-x

  日期：2016.2

  3-Heterocyclic coumarins were prepared in one-pot three-component reaction without catalyst. The mixture of salicylaldehydes, ethyl cyanoacetate, and o-aminophenols or o-phenylenediamines in refluxing n-butanol gave title compounds with good yields and high purity. Short reaction time, mild reaction condition, simple workup, and less waste are significant advantages of the presented method.

  在不使用催化剂的情况下，通过单锅三组分反应制备了 3-杂环香豆素。水杨醛、氰乙酸乙酯和邻氨基苯酚或邻苯二胺在回流正丁醇中的混合物得到了收率高、纯度高的标题化合物。该方法具有反应时间短、反应条件温和、操作简单、浪费少等显著优点。