5-[2-(3,4,5-Trimethoxyphenyl)ethenyl]-1,3,4-thiadiazol-2-amine | 88743-00-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[2-(3,4,5-Trimethoxyphenyl)ethenyl]-1,3,4-thiadiazol-2-amine
• 英文别名: 5-[2-(3,4,5-trimethoxyphenyl)ethenyl]-1,3,4-thiadiazol-2-amine
• CAS: 88743-00-4
• 化学式: C₁₃H₁₅N₃O₃S
• 分子量: 293.346
• InChiKey: NLLIVNAUYZOXBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-[2-(3,4,5-Trimethoxyphenyl)ethenyl]-1,3,4-thiadiazol-2-amine 、 藜芦酸 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 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以69.5%的产率得到(E)-3,4-dimethoxy-N-(5-(3,4,5-trimethoxystyryl)-1,3,4-thiadiazol-2-yl)benzamide
  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：

  3,4,5-三甲氧基肉桂酸 、 氨基硫脲 在 三氯氧磷 、 potassium hydroxide 作用下， 反应 1.0h， 生成 5-[2-(3,4,5-Trimethoxyphenyl)ethenyl]-1,3,4-thiadiazol-2-amine
  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

文献信息

• Synthesis, biological evaluation and molecular modeling of 1,3,4-thiadiazol-2-amide derivatives as novel antitubulin agents
  作者：Yu-Jing Li、Ya-Juan Qin、Jigar A. Makawana、Yan-Ting Wang、Yan-Qing Zhang、Ya-Liang Zhang、Meng-Ru Yang、Ai-Qin Jiang、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2014.05.017

  日期：2014.8

  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.