6-(2-bromo-3,4,5-trimethoxyphenyl)-2-methyl-imidazo[2,1-b]thiazole | 1359986-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-(2-bromo-3,4,5-trimethoxyphenyl)-2-methyl-imidazo[2,1-b]thiazole
• CAS: 1359986-92-7
• 化学式: C₁₅H₁₅BrN₂O₃S
• 分子量: 383.266
• InChiKey: NOUWXYUMKCYYCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.99
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-(2-bromo-3,4,5-trimethoxyphenyl)-2-methyl-imidazo[2,1-b]thiazole 在 哌啶 、 三氯氧磷 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 5.0h， 生成 3-[[6-(2-bromo-3,4,5-trimethoxyphenyl)-2-methylimidazo[2,1-b][1,3]thiazol-5-yl]methylidene]-5-methoxy-1H-indol-2-one
  参考文献：
  名称：

  Substituted 3-(5-Imidazo[2,1-b]thiazolylmethylene)-2-indolinones and Analogues: Synthesis, Cytotoxic Activity, and Study of the Mechanism of Action

  摘要：

  The synthesis of substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones and analogues is reported. Their cytotoxic activity was evaluated according to protocols available at the National Cancer Institute (NCI), Bethesda, MD. The action of selected compounds was examined for potential inhibition of tubulin assembly in comparison with the potent colchicine site agent combretastatin A-4. The most potent compounds also strongly and selectively inhibited the phosphorylation of the oncoprotein kinase Akt in cancer cells. The effect of the most interesting compounds was examined on the growth of HT-29 colon cancer cells. These compounds caused the cells to arrest in the G2/M phase of the cell cycle, as would be expected for inhibitors of tubulin assembly.

  DOI：

  10.1021/jm2012694
• 作为产物：
  描述：

  2-氨基-5-甲基噻唑 、 3',4',5'-三甲氧基苯乙酮 在 溴 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 5.0h， 以28%的产率得到2-methyl-6-(3,4,5-trimethoxyphenyl)imidazo[2,1-b]thiazole
  参考文献：
  名称：

  Substituted 3-(5-Imidazo[2,1-b]thiazolylmethylene)-2-indolinones and Analogues: Synthesis, Cytotoxic Activity, and Study of the Mechanism of Action

  摘要：

  The synthesis of substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones and analogues is reported. Their cytotoxic activity was evaluated according to protocols available at the National Cancer Institute (NCI), Bethesda, MD. The action of selected compounds was examined for potential inhibition of tubulin assembly in comparison with the potent colchicine site agent combretastatin A-4. The most potent compounds also strongly and selectively inhibited the phosphorylation of the oncoprotein kinase Akt in cancer cells. The effect of the most interesting compounds was examined on the growth of HT-29 colon cancer cells. These compounds caused the cells to arrest in the G2/M phase of the cell cycle, as would be expected for inhibitors of tubulin assembly.

  DOI：

  10.1021/jm2012694