2-bromo-3,4,5-trimethoxy cinnamic acid | 115105-86-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-bromo-3,4,5-trimethoxy cinnamic acid
• 英文别名: 3-(2-Bromo-3,4,5-trimethoxyphenyl)prop-2-enoic acid
• CAS: 115105-86-7
• 化学式: C₁₂H₁₃BrO₅
• 分子量: 317.136
• InChiKey: KVWPCSGGAVOLHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  431.5±40.0 °C(Predicted)
• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-bromo-3,4,5-trimethoxy cinnamic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 (E)-2-bromo-N-(5-(2-bromo-3,4,5-trimethoxystyryl)-1,3,4-thiadiazol-2-yl)-3,4,5-trimethoxybenzamide
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modeling of 1,3,4-thiadiazol-2-amide derivatives as novel antitubulin agents

  摘要：

  A series of 1,3,4-thiadiazol-2-amide derivatives (6a-w) were designed and synthesized as potential inhibitors of tubulin polymerization and as anticancer agents. The in vitro anticancer activities of these compounds were evaluated against three cancer cell lines by the MTT method. Among all the designed compounds, compound 6f exhibited the most potent anticancer activity against A549, MCF-7 and HepG2 cancer cell lines with IC₅₀ values of 0.03 μM, 0.06 μM and 0.05 μM, respectively. Compound 6f also exhibited significant tubulin polymerization inhibitory activity (IC₅₀=1.73 μM), which was superior to the positive control. The obtained results, along with a 3D-QSAR study and molecular docking that were used for investigating the probable binding mode, could provide an important basis for further optimization of compound 6f as a novel anticancer agent.

  DOI：

  10.1016/j.bmc.2014.05.017
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 哌啶 、 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 15.0h， 生成 2-bromo-3,4,5-trimethoxy cinnamic acid
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modeling of 1,3,4-thiadiazol-2-amide derivatives as novel antitubulin agents

  摘要：

  A series of 1,3,4-thiadiazol-2-amide derivatives (6a-w) were designed and synthesized as potential inhibitors of tubulin polymerization and as anticancer agents. The in vitro anticancer activities of these compounds were evaluated against three cancer cell lines by the MTT method. Among all the designed compounds, compound 6f exhibited the most potent anticancer activity against A549, MCF-7 and HepG2 cancer cell lines with IC₅₀ values of 0.03 μM, 0.06 μM and 0.05 μM, respectively. Compound 6f also exhibited significant tubulin polymerization inhibitory activity (IC₅₀=1.73 μM), which was superior to the positive control. The obtained results, along with a 3D-QSAR study and molecular docking that were used for investigating the probable binding mode, could provide an important basis for further optimization of compound 6f as a novel anticancer agent.

  DOI：

  10.1016/j.bmc.2014.05.017