6-Methoxy-imidazo[2,1-b]thiazole-5-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并噻唑类
• 英文名称: 6-Methoxy-imidazo[2,1-b]thiazole-5-carbaldehyde
• 英文别名: 6-Methoxyimidazo[2,1-b][1,3]thiazole-5-carbaldehyde
• 化学式: C₇H₆N₂O₂S
• mdl: MFCD06660547
• 分子量: 182.203
• InChiKey: BQZZVYHLXZYNIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-氟吲哚-2-酮 、 6-Methoxy-imidazo[2,1-b]thiazole-5-carbaldehyde 在 哌啶 作用下， 以 甲醇 为溶剂， 生成 NSC 748112
  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：

  sodium methylate 、 6-氯咪唑并[2,1-b][1,3]噻唑-5-甲醛 在 假硫代乙内酰脲 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以50%的产率得到6-Methoxy-imidazo[2,1-b]thiazole-5-carbaldehyde
  参考文献：
  名称：

  Synthesis and cardiotonic activity of imidazo[2,l-b]thiazoles bearing a lactam ring

  摘要：

  This paper describes the synthesis of 6-substituted imidazo[2,1-b] thiazoles with a lactam ring connected, by means of a methine group, to the 5-position. The pharmacological results show that interesting cardiotonic activity is obtained when the lactam ring is pseudothiohydantoin (8) or barbituric acid (9). Even the substituent at position 6 plays an important role in the pharmacological behavior of these derivatives. The following activity rank order was observed: phenyl > methyl > chlorine.

  DOI：

  10.1016/0223-5234(96)89164-1

文献信息

• Substituted 3-(5-Imidazo[2,1-<i>b</i>]thiazolylmethylene)-2-indolinones and Analogues: Synthesis, Cytotoxic Activity, and Study of the Mechanism of Action
  作者：Aldo Andreani、Massimiliano Granaiola、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Lucilla Varoli、Natalia Calonghi、Concettina Cappadone、Giovanna Farruggia、Claudio Stefanelli、Lanfranco Masotti、Tam L. Nguyen、Ernest Hamel、Robert H. Shoemaker

  DOI：10.1021/jm2012694

  日期：2012.3.8

  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.
• Synthesis and cardiotonic activity of imidazo[2,l-b]thiazoles bearing a lactam ring
  作者：A Andreani、M Rambaldi、A Leoni、A Locatelli、R Bossa、M Chiericozzi、I Galatulas、G Salvatore

  DOI：10.1016/0223-5234(96)89164-1

  日期：1996.1

  This paper describes the synthesis of 6-substituted imidazo[2,1-b] thiazoles with a lactam ring connected, by means of a methine group, to the 5-position. The pharmacological results show that interesting cardiotonic activity is obtained when the lactam ring is pseudothiohydantoin (8) or barbituric acid (9). Even the substituent at position 6 plays an important role in the pharmacological behavior of these derivatives. The following activity rank order was observed: phenyl > methyl > chlorine.