3-(5',6'-dimethylbenzimidazol-20-yl)coumarin | 875006-90-9

• 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: 3-(5',6'-dimethylbenzimidazol-20-yl)coumarin
• 英文别名: 3-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)-2H-chromen-2-one；3-(5,6-dimethyl-1H-benzimidazol-2-yl)chromen-2-one
• CAS: 875006-90-9
• 化学式: C₁₈H₁₄N₂O₂
• 分子量: 290.321
• InChiKey: PFXLYRWGECOECL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  香豆素-3-羧酸 在 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 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 3-(5',6'-dimethylbenzimidazol-20-yl)coumarin
  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

• Coumarins hinged directly on benzimidazoles and their ribofuranosides to inhibit hepatitis C virus
  作者：Shwu-Chen Tsay、Jih Ru Hwu、Raghunath Singha、Wen-Chieh Huang、Yung Hsiung Chang、Ming-Hua Hsu、Fa-kuen Shieh、Chun-Cheng Lin、Kuo Chu Hwang、Jia-Cherng Horng、Erik De Clercq、Inge Vliegen、Johan Neyts

  DOI：10.1016/j.ejmech.2013.02.008

  日期：2013.5

  A new compound library that contained 20 hinged benzimidazole coumarin hybrids and their beta-D-ribofuranosides was established. The anti-hepatitis C virus (HCV) activity of all novel coumarin derivatives, which were obtained by use of organic synthetic methods, was tested. Two of these hybrids exhibited appealing EC50 values of as low as 3.0 and 5.5 mu M. The best selectivity index was 14. The incorporation of a D-ribofuranose into the hinged hybrids provided the corresponding nucleosides with the beta configuration, one of which inhibited HCV replication with an EC50 value of 20 mu M. Additionally, the structure activity relationship is elucidated on the basis of the functional groups that were attached to the nuclei of benzimidazole, coumarin, and ribofuranose of the hybrids. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Design, Synthesis, and<i>In Vitro</i>Evaluation of Novel 3, 7-Disubstituted Coumarin Derivatives as Potent Anticancer Agents
  作者：Yubin Wang、Haitao Liu、Peng Lu、Rui Mao、Xiaojian Xue、Chen Fan、Jinxiong She

  DOI：10.1111/cbdd.12531

  日期：2015.10

  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.