2,6-dimethylimidazo[2,1-b][1,3,4]thiadiazole-5-carboxaldehyde | 294179-25-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,6-dimethylimidazo[2,1-b][1,3,4]thiadiazole-5-carboxaldehyde
• 英文别名: 2,6-Dimethylimidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde
• CAS: 294179-25-2
• 化学式: C₇H₇N₃OS
• mdl: MFCD11886814
• 分子量: 181.218
• InChiKey: ZJJUIACYGXTGNM-UHFFFAOYSA-N

物化性质

• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  75.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-dimethylimidazo[2,1-b][1,3,4]thiadiazole-5-carboxaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以75%的产率得到2,6-dimethyl-5-hydroxymethylimidazo[2,1-b][1,3,4]thiadiazole
  参考文献：
  名称：

  Andreani, Aldo; Leoni, Alberto; Locatelli, Alessandra, Arzneimittel-Forschung/Drug Research, 2000, vol. 50, # 6, p. 550 - 553

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2-imino-5-methyl-3-[1,3,4]thiadiazolyl)acetone hydrochloride 在 ammonium hydroxide 、 氢溴酸 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 反应 9.0h， 生成 2,6-dimethylimidazo[2,1-b][1,3,4]thiadiazole-5-carboxaldehyde
  参考文献：
  名称：

  Andreani, Aldo; Leoni, Alberto; Locatelli, Alessandra, Arzneimittel-Forschung/Drug Research, 2000, vol. 50, # 6, p. 550 - 553

  摘要：

  DOI：

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.
• Antitumor Activity of New Substituted 3-(5-Imidazo[2,1-<i>b</i>]thiazolylmethylene)-2-indolinones and 3-(5-Imidazo[2,1-<i>b</i>]thiadiazolylmethylene)-2-indolinones: Selectivity against Colon Tumor Cells and Effect on Cell Cycle-Related Events
  作者：Aldo Andreani、Silvia Burnelli、Massimiliano Granaiola、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Lucilla Varoli、Natalia Calonghi、Concettina Cappadone、Manuela Voltattorni、Maddalena Zini、Claudio Stefanelli、Lanfranco Masotti、Robert H. Shoemaker

  DOI：10.1021/jm800827q

  日期：2008.12.11

  The synthesis of new 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones and 3-(5-imidazo[2,1-b]thiadiazolylmethylene)-2-indolinones is reported. The antitumor activity was evaluated according to the protocols available at the National Cancer Institute (NCI), Bethesda, MD. To investigate the mechanism of action of the most potent antitumor agent of this series, its effect on growth of HT-29 colon carcinoma cells was studied. Its ability to inhibit cellular proliferation was mediated by cell cycle arrest at the G2/M phase, accompanied by inhibition of ornithine decarboxylase (ODC), the limiting enzyme of polyamine synthesis, and followed by induction of apoptosis.