2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylate | 1609584-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylate
• CAS: 1609584-70-4
• 化学式: C₁₅H₁₅N₃O₆
• 分子量: 333.301
• InChiKey: BALKHNOAQFCFIU-UHFFFAOYSA-N

物化性质

• 沸点：
  573.2±50.0 °C(predicted)
• 密度：
  1.47±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  105.72
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylate 、 3-甲基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 2-((Z)-2-(3-methylstyryl)-5-nitro-1H-imidazol-1-yl)ethyl 2,3-dihydro-1,4-benzodioxine-5-carboxylate
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular docking studies of novel 2-styryl-5-nitroimidazole derivatives containing 1,4-benzodioxan moiety as FAK inhibitors with anticancer activity

  摘要：

  A series of 2-styryl-5-nitroimidazole derivatives containing 1,4-benzodioxan moiety (3a-3r) has been designed, synthesized and their biological activities were also evaluated as potential antiproliferation and focal adhesion kinase (FAK) inhibitors. Among all the compounds, 3p showed the most potent activity in vitro which inhibited the growth of A549 with IC50 value of 3.11 mu M and Hela with IC50 value of 2.54 mu M respectively. Compound 3p also exhibited significant FAK inhibitory activity (IC50 = 0.45 mu M). Docking simulation was performed for compound 3p into the FAK structure active site to determine the probable binding model. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.005
• 作为产物：
  描述：

  苯甲酸,二羟基- 在 甲醇 、 氯化亚砜 、 硫酸 、 potassium carbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 22.0h， 生成 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylate
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular docking studies of novel 2-styryl-5-nitroimidazole derivatives containing 1,4-benzodioxan moiety as FAK inhibitors with anticancer activity

  摘要：

  A series of 2-styryl-5-nitroimidazole derivatives containing 1,4-benzodioxan moiety (3a-3r) has been designed, synthesized and their biological activities were also evaluated as potential antiproliferation and focal adhesion kinase (FAK) inhibitors. Among all the compounds, 3p showed the most potent activity in vitro which inhibited the growth of A549 with IC50 value of 3.11 mu M and Hela with IC50 value of 2.54 mu M respectively. Compound 3p also exhibited significant FAK inhibitory activity (IC50 = 0.45 mu M). Docking simulation was performed for compound 3p into the FAK structure active site to determine the probable binding model. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.005