3-(3-trifluoromethylphenyl)-6-phenylimidazo[2,1-b]thiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(3-trifluoromethylphenyl)-6-phenylimidazo[2,1-b]thiazole
• 英文别名: 6-Phenyl-3-[3-(trifluoromethyl)phenyl]imidazo[2,1-b][1,3]thiazole；6-phenyl-3-[3-(trifluoromethyl)phenyl]imidazo[2,1-b][1,3]thiazole
• 化学式: C₁₈H₁₁F₃N₂S
• 分子量: 344.36
• InChiKey: CWHJFZCXSCTEDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  间三氟甲基苯乙酮 在 碘 作用下， 以 乙醇 为溶剂， 100.0 ℃ 、1.72 MPa 条件下， 反应 8.0h， 生成 3-(3-trifluoromethylphenyl)-6-phenylimidazo[2,1-b]thiazole
  参考文献：
  名称：

  Synthesis and anticancer evaluation of 3-aryl-6-phenylimidazo[2,1-b]thiazoles

  摘要：

  A series of new 3,6-diphenylimidazo[2,1-b] thiazole derivatives (4a-l) are synthesized and evaluated for their anticancer activity. Some of the synthesized compounds have shown potent anti-proliferative activity against HeLa, MDA-MB-231, A549 and THP1 human cancer cell lines. Among the active compounds, 3-(3-trifluoromethylphenyl)-6-phenylimidazo[2,1-b] thiazole (4j) has caused significant cytotoxicity in HeLa cells, with IC50 as low as 6.5 mu M. Compound 4j has induced caspase-3 and caspase- 8 activation, leading to an apoptotic cell death. FACS analysis has revealed that compound 4j arrests cells in G0/ G1 phase. The presence of 3-(3-trifluoromethylphenyl)-or 3-(3-chlorophenyl)-substituent, in that order, on the 6-phenylimidazo[2,1-b] thiazole impacts more positively than other aryl-substituents, on the anti-proliferative properties of these compounds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.030

文献信息

• Synthesis and anticancer evaluation of 3-aryl-6-phenylimidazo[2,1-b]thiazoles
  作者：Satish Koppireddi、Deepika Raj Kumari Chilaka、Sreenivas Avula、Jayaram Reddy Komsani、Srigiridhar Kotamraju、Rambabu Yadla

  DOI：10.1016/j.bmcl.2014.10.030

  日期：2014.12

  A series of new 3,6-diphenylimidazo[2,1-b] thiazole derivatives (4a-l) are synthesized and evaluated for their anticancer activity. Some of the synthesized compounds have shown potent anti-proliferative activity against HeLa, MDA-MB-231, A549 and THP1 human cancer cell lines. Among the active compounds, 3-(3-trifluoromethylphenyl)-6-phenylimidazo[2,1-b] thiazole (4j) has caused significant cytotoxicity in HeLa cells, with IC50 as low as 6.5 mu M. Compound 4j has induced caspase-3 and caspase- 8 activation, leading to an apoptotic cell death. FACS analysis has revealed that compound 4j arrests cells in G0/ G1 phase. The presence of 3-(3-trifluoromethylphenyl)-or 3-(3-chlorophenyl)-substituent, in that order, on the 6-phenylimidazo[2,1-b] thiazole impacts more positively than other aryl-substituents, on the anti-proliferative properties of these compounds. (C) 2014 Elsevier Ltd. All rights reserved.