(5Z)-5-(4-bromobenzylidene)-3-(prop-2-yn-1-yl)-1,3-thiazolidine-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (5Z)-5-(4-bromobenzylidene)-3-(prop-2-yn-1-yl)-1,3-thiazolidine-2,4-dione
• 英文别名: (5Z)-5-[(4-bromophenyl)methylidene]-3-prop-2-ynyl-1,3-thiazolidine-2,4-dione
• 化学式: C₁₃H₈BrNO₂S
• 分子量: 322.182
• InChiKey: HCSAZIFYYLLMPK-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(azidomethyl)-6-methyl-2H-chromen-2-one 、 (5Z)-5-(4-bromobenzylidene)-3-(prop-2-yn-1-yl)-1,3-thiazolidine-2,4-dione 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 以97 %的产率得到(5Z)-5-(4-bromobenzylidene-3-((1-(6-methyl-2-oxo-2H-chromen-4-yl)-methyl)-1H-1,2,3-triazol-4-yl)methyl)-thiazolidine-2,4-dione
  参考文献：
  名称：

  Coumarin-4-yl‐1,2,3‐triazol‐4-yl-methyl-thiazolidine-2,4-diones: Synthesis, glucose uptake activity and cytotoxic evaluation

  摘要：

  Thiazolidinedione (TZD) based medications have demonstrated to enhance the insulin sensitivity control, hyperglycemia, and lipid metabolism in patients with type 2 diabetes. Hence, in this study, a new series of novel coumarin-4-yl-1,2,3-triazol-4-yl-methyl-thiazolidine-2,4-diones (TZD1-TZD18) were synthesized via copper (I)-catalyzed azide-alkyne cycloaddition "Click Chemistry". The synthesized compounds were evaluated for their glucose uptake assay and in vitro cytotoxicity against HEK-293 (human embryonic kidney) cells which were compared with the standard drug Pioglitazone. Further, molecular docking analysis of these compounds was carried out to explain the in vitro results with PPARγ (PDB ID: 3CS8) and to better understand the bonding interactions with the target protein. The outcomes of in vitro assessment, molecular docking, and pharmacokinetics of the title compounds were revealed to be highly correlated. Interestingly, the compounds TZD4, TZD10, TZD14 and TZD16 were most efficient in lowering the blood glucose level compared with standard drug.

  DOI：

  10.1016/j.bioorg.2022.106235
• 作为产物：
  描述：

  3-溴丙炔 、 5-(4-bromobenzylidene)thiazolidine-2,4-dione 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以90 %的产率得到(5Z)-5-(4-bromobenzylidene)-3-(prop-2-yn-1-yl)-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  Coumarin-4-yl‐1,2,3‐triazol‐4-yl-methyl-thiazolidine-2,4-diones: Synthesis, glucose uptake activity and cytotoxic evaluation

  摘要：

  Thiazolidinedione (TZD) based medications have demonstrated to enhance the insulin sensitivity control, hyperglycemia, and lipid metabolism in patients with type 2 diabetes. Hence, in this study, a new series of novel coumarin-4-yl-1,2,3-triazol-4-yl-methyl-thiazolidine-2,4-diones (TZD1-TZD18) were synthesized via copper (I)-catalyzed azide-alkyne cycloaddition "Click Chemistry". The synthesized compounds were evaluated for their glucose uptake assay and in vitro cytotoxicity against HEK-293 (human embryonic kidney) cells which were compared with the standard drug Pioglitazone. Further, molecular docking analysis of these compounds was carried out to explain the in vitro results with PPARγ (PDB ID: 3CS8) and to better understand the bonding interactions with the target protein. The outcomes of in vitro assessment, molecular docking, and pharmacokinetics of the title compounds were revealed to be highly correlated. Interestingly, the compounds TZD4, TZD10, TZD14 and TZD16 were most efficient in lowering the blood glucose level compared with standard drug.

  DOI：

  10.1016/j.bioorg.2022.106235

文献信息

• Coumarin-4-yl‐1,2,3‐triazol‐4-yl-methyl-thiazolidine-2,4-diones: Synthesis, glucose uptake activity and cytotoxic evaluation
  作者：Tukaram V. Metre、Barnabas Kodasi、Praveen K. Bayannavar、Lokesh Bheemayya、Vishwa B. Nadoni、Swati R. Hoolageri、Arun K. Shettar、Shrinivas D. Joshi、Vijay M. Kumbar、Ravindra R. Kamble

  DOI：10.1016/j.bioorg.2022.106235

  日期：2023.1

  Thiazolidinedione (TZD) based medications have demonstrated to enhance the insulin sensitivity control, hyperglycemia, and lipid metabolism in patients with type 2 diabetes. Hence, in this study, a new series of novel coumarin-4-yl-1,2,3-triazol-4-yl-methyl-thiazolidine-2,4-diones (TZD1-TZD18) were synthesized via copper (I)-catalyzed azide-alkyne cycloaddition "Click Chemistry". The synthesized compounds were evaluated for their glucose uptake assay and in vitro cytotoxicity against HEK-293 (human embryonic kidney) cells which were compared with the standard drug Pioglitazone. Further, molecular docking analysis of these compounds was carried out to explain the in vitro results with PPARγ (PDB ID: 3CS8) and to better understand the bonding interactions with the target protein. The outcomes of in vitro assessment, molecular docking, and pharmacokinetics of the title compounds were revealed to be highly correlated. Interestingly, the compounds TZD4, TZD10, TZD14 and TZD16 were most efficient in lowering the blood glucose level compared with standard drug.