3-(4-chlorophenyl)-6-phenylimidazo[2,1-b]thiazole | 56921-54-1

• 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-(4-chlorophenyl)-6-phenylimidazo[2,1-b]thiazole
• 英文别名: 3-(4-chloro-phenyl)-6-phenyl-imidazo[2,1-b]thiazole；3-(4-Chlorophenyl)-6-phenylimidazo[2,1-b][1,3]thiazole
• CAS: 56921-54-1
• 化学式: C₁₇H₁₁ClN₂S
• 分子量: 310.807
• InChiKey: JAPMGEFLIPVQKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对氯苯乙酮 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-(4-chlorophenyl)-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

• Approach for 2-(arylthio)imidazoles and imidazo[2,1-b]thiazoles from imidazo[2,1-b][1,3,4]thiadiazoles by ring-opening and -reconstruction
  作者：Benyi Shi、Zhouhe Zhu、Yi-Shuo Zhu、Dagang Zhou、Jinyuan Wang、Panpan Zhou、Huanwang Jing

  DOI：10.1039/c6ob00102e

  日期：——

  synthesis of imidazo[2,1-b]thiazole derivatives has been developed and proceeds via a ring-opening and ring-closing reconstruction of imidazo[2,1-b][1,3,4]thiadiazoles with phenylacetylene in the presence of potassium tert-butoxide (t-BuOK) under very mild reaction conditions. A proposed mechanism is calculated computationally using a DFT method at the B3LYP/6-31+G(d,p) level. The imidazo[2,1-b][1,3,4]thiadiazoles

  咪唑并[2,1- b ]噻唑衍生物的高效一锅合成已得到开发，并通过咪唑并[2,1- b ] [1,3,4]噻二唑的开环和闭环重构而进行在非常温和的反应条件下，在叔丁醇钾（t -BuOK）存在下，用苯乙炔与苯乙炔 在B3LYP / 6-31 + G（d，p）级别上使用DFT方法以计算方式计算了一种建议的机制。咪唑并[2,1- b ] [1,3,4]噻二唑也成功地转化为一系列的2-（芳硫基）-1 H-咪唑，使用的是芳基卤化物和乙酰丙酮铜（II）（Cu（ acac）2）在微波辐射条件下作为催化剂。这些反应的关键特征是使用现成的试剂，操作简单，方便地使用新的杂环合成子以及具有功能基团相容性的多种底物。
• Patra,M. et al., Journal of the Indian Chemical Society, 1974, vol. 51, p. 1031 - 1034
  作者：Patra,M. et al.

  DOI：——

  日期：——