6-(4-Chlorophenyl)-2-ethylimidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde | 1175882-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-(4-Chlorophenyl)-2-ethylimidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde
• CAS: 1175882-47-9
• 化学式: C₁₃H₁₀ClN₃OS
• 分子量: 291.761
• InChiKey: UNYZZOFKDCZRCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  2,4-噻唑烷二酮 、 6-(4-Chlorophenyl)-2-ethylimidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde 在 乙酸哌啶酯 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以92%的产率得到5-{[6-(4-chlorophenyl)-2-ethylimidazo[2,1-b][1,3,4]thiadiazol-5-yl]methylene}-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis, Hypoglycaemic, Hypolipidemic and PPARγ Agonist Activities of 5-(2-Alkyl/aryl-6-Arylimidazo[2,1-b][1,3,4]thiadiazol-5-yl)methylene-1,3-Thiazolidinediones

  摘要：

  A novel series of 5‐(2‐alkyl/aryl‐6‐arylimidazo[2,1‐b][1,3,4]thiadiazol‐5‐yl)methylene‐1,3‐thiazolidinediones were synthesized as possible PPARγ agonists. The structures of these target molecules were established by spectral and analytical data. All the newly synthesized compounds were screened for their in vivo hypoglycaemic and hypolipidemic activity in male Wistar rats. Further, compounds with good activity were screened for PPARγ agonist activity. Among the screened compounds, 5‐{[2‐Cyclohexyl‐6‐(4‐methoxyphenyl)imidazo[2,1‐b] [1,3,4]thiadiazol‐5‐yl]methylene}‐1,3‐thiazolidine‐2,4‐dione (3i) exhibits promising hypoglycaemic and hypolipidemic activity via potential PPARγ agonist activity.

  DOI：

  10.1111/cbdd.12140
• 作为产物：
  描述：

  2'-溴-4-氯苯乙酮 在 sodium carbonate 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 6-(4-Chlorophenyl)-2-ethylimidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde
  参考文献：
  名称：

  Synthesis, Hypoglycaemic, Hypolipidemic and PPARγ Agonist Activities of 5-(2-Alkyl/aryl-6-Arylimidazo[2,1-b][1,3,4]thiadiazol-5-yl)methylene-1,3-Thiazolidinediones

  摘要：

  A novel series of 5‐(2‐alkyl/aryl‐6‐arylimidazo[2,1‐b][1,3,4]thiadiazol‐5‐yl)methylene‐1,3‐thiazolidinediones were synthesized as possible PPARγ agonists. The structures of these target molecules were established by spectral and analytical data. All the newly synthesized compounds were screened for their in vivo hypoglycaemic and hypolipidemic activity in male Wistar rats. Further, compounds with good activity were screened for PPARγ agonist activity. Among the screened compounds, 5‐{[2‐Cyclohexyl‐6‐(4‐methoxyphenyl)imidazo[2,1‐b] [1,3,4]thiadiazol‐5‐yl]methylene}‐1,3‐thiazolidine‐2,4‐dione (3i) exhibits promising hypoglycaemic and hypolipidemic activity via potential PPARγ agonist activity.

  DOI：

  10.1111/cbdd.12140

文献信息

• Synthesis and antiproliferative activity of imidazo[2,1- b ][1,3,4]thiadiazole derivatives
  作者：Sujeet Kumar、Vidya Gopalakrishnan、Mahesh Hegde、Vivek Rana、Sharad S. Dhepe、Sureshbabu A. Ramareddy、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Mrinal Srivastava、Sathees C. Raghavan、Subhas S. Karki

  DOI：10.1016/j.bmcl.2014.08.032

  日期：2014.10

  6-substituted imidazo[2,1-b][1,3,4]thiadiazole derivatives have been prepared and were tested for antiproliferative activity on cancer cells at the National Cancer Institute. Results showed that molecules with a benzyl group at position 2, exhibited an increase in activity for the introduction of a formyl group at the 5 position. The compound 2-benzyl-5-formyl-6-(4-bromophenyl)imidazo[2,1-b][1,3,4]thiadiazole

  已经制备了一系列的2,5,6-取代的咪唑并[2,1- b ] [1,3,4]噻二唑衍生物，并在美国国家癌症研究所测试了其对癌细胞的抗增殖活性。结果表明，在2位具有苄基的分子表现出在5位引入甲酰基的活性增加。化合物2-苄基-5-甲酰基-6-（4-溴苯基）咪唑并[2,1- b ] [1,3,4]噻二唑22已通过各种分子和细胞生物学研究选择了理解作用机理的化合物。从细胞周期评估分析，通过流式细胞术分析线粒体膜电位和膜联蛋白V-FITC，ROS产生以及凋亡和DNA修复蛋白表达获得的结果表明，化合物22通过激活细胞凋亡的外在途径诱导细胞毒性。影响细胞周期进程。