3-[5-bromo-2-(4-chlorobenzyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl]-2H-chromen-2-one | 1620897-80-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-[5-bromo-2-(4-chlorobenzyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl]-2H-chromen-2-one
• 英文别名: 3-[5-Bromo-2-[(4-chlorophenyl)methyl]imidazo[2,1-b][1,3,4]thiadiazol-6-yl]chromen-2-one；3-[5-bromo-2-[(4-chlorophenyl)methyl]imidazo[2,1-b][1,3,4]thiadiazol-6-yl]chromen-2-one
• CAS: 1620897-80-4
• 化学式: C₂₀H₁₁BrClN₃O₂S
• 分子量: 472.749
• InChiKey: RSDYECVSUHDIOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基-5-(4-氯苄基)-1,3,4-噻二唑 在 溴 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 3-[5-bromo-2-(4-chlorobenzyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl]-2H-chromen-2-one
  参考文献：
  名称：

  2-(4-Chlorobenzyl)-6-arylimidazo[2,1-b][1,3,4]thiadiazoles: Synthesis, cytotoxic activity and mechanism of action

  摘要：

  The cytotoxic activity of a new series of 2-(4'-chlorobenzyl)-5,6-disubstituted imidazo[2,1-b][1,3,4]thiadiazoles against different human and murine cancer cell lines is reported. Among the tested compounds, two derivatives namely 2-(4-chlorobenzyl)-6-(2-oxo-2H-chromen-3-yl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde 4i and 2-(4-chlorobenzyl)-6-(2-oxo-2H-chromen-3-yl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl thiocyanate 5i emerged as the most potent against all the cell lines. To investigate the mechanism of action, we selected compounds 4i for cell cycle study, analysis of mitochondrial membrane potential and Annexin V-FITC flow cytometric analysis and DNA fragmentation assay. Results showed that 4i induced cytotoxicity by inducing apoptosis without arresting the cell cycle.

  DOI：

  10.1016/j.ejmech.2014.07.054

文献信息

• 2-(4-Chlorobenzyl)-6-arylimidazo[2,1-b][1,3,4]thiadiazoles: Synthesis, cytotoxic activity and mechanism of action
  作者：Sujeet Kumar、Mahesh Hegde、Vidya Gopalakrishnan、Vinaya Kumar Renuka、Sureshbabu A. Ramareddy、Erik De Clercq、Dominique Schols、Anil Kumar Gudibabande Narasimhamurthy、Sathees C. Raghavan、Subhas S. Karki

  DOI：10.1016/j.ejmech.2014.07.054

  日期：2014.9

  The cytotoxic activity of a new series of 2-(4'-chlorobenzyl)-5,6-disubstituted imidazo[2,1-b][1,3,4]thiadiazoles against different human and murine cancer cell lines is reported. Among the tested compounds, two derivatives namely 2-(4-chlorobenzyl)-6-(2-oxo-2H-chromen-3-yl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde 4i and 2-(4-chlorobenzyl)-6-(2-oxo-2H-chromen-3-yl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl thiocyanate 5i emerged as the most potent against all the cell lines. To investigate the mechanism of action, we selected compounds 4i for cell cycle study, analysis of mitochondrial membrane potential and Annexin V-FITC flow cytometric analysis and DNA fragmentation assay. Results showed that 4i induced cytotoxicity by inducing apoptosis without arresting the cell cycle.