5[(6-chloro-4-oxo-4H-chromen-3yl)methyl]thiazolidine-2,4-dione | 1616476-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5[(6-chloro-4-oxo-4H-chromen-3yl)methyl]thiazolidine-2,4-dione
• 英文别名: 5-[(6-Chloro-4-oxochromen-3-yl)methyl]-1,3-thiazolidine-2,4-dione；5-[(6-chloro-4-oxochromen-3-yl)methyl]-1,3-thiazolidine-2,4-dione
• CAS: 1616476-73-3
• 化学式: C₁₃H₈ClNO₄S
• 分子量: 309.73
• InChiKey: HFARBHYZTFLIOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-氯-3-甲酰基色酮 在 palladium 10% on activated carbon 、 氢气 、 sodium acetate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0~140.0 ℃ 、206.85 kPa 条件下， 反应 12.0h， 生成 5[(3,4-dihydro-6-chloro-4-oxo-4H-chromen-3-yl)methyl]thiazolidine-2,4-dione 、 5[(6-chloro-4-oxo-4H-chromen-3yl)methyl]thiazolidine-2,4-dione
  参考文献：
  名称：

  Thiazolidine-2,4-diones derivatives as PPAR-γ agonists: Synthesis, molecular docking, in vitro and in vivo antidiabetic activity with hepatotoxicity risk evaluation and effect on PPAR-γ gene expression

  摘要：

  A library of conjugates of chromones and 2,4-thiazolidinedione has been synthesized by Knoevenagel condensation followed by reduction using hydrogen gas and Pd/C as a catalyst. Compounds 5c and 5e were most effective in lowering the blood glucose level comparable to standard drug pioglitazone. Compound 5e exhibited potent PPAR-gamma transactivation of 48.72% in comparison to pioglitazone (62.48%). All the molecules showed good glide score against the PPAR-gamma target in molecular docking study. PPAR-gamma gene expression was significantly increased by compound 5e (2.56-fold) in comparison to standard drug pioglitazone. Compounds 5e and 5c did not cause any damage to the liver and may be considered as promising candidates for the development of new antidiabetic agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.034

文献信息

• Thiazolidine-2,4-diones derivatives as PPAR-γ agonists: Synthesis, molecular docking, in vitro and in vivo antidiabetic activity with hepatotoxicity risk evaluation and effect on PPAR-γ gene expression
  作者：Syed Nazreen、Mohammad Sarwar Alam、Hinna Hamid、Mohammad Shahar Yar、Abhijeet Dhulap、Perwez Alam、M.A.Q. Pasha、Sameena Bano、Mohammad Mahboob Alam、Saqlain Haider、Chetna Kharbanda、Yakub Ali、K.K. Pillai

  DOI：10.1016/j.bmcl.2014.05.034

  日期：2014.7

  A library of conjugates of chromones and 2,4-thiazolidinedione has been synthesized by Knoevenagel condensation followed by reduction using hydrogen gas and Pd/C as a catalyst. Compounds 5c and 5e were most effective in lowering the blood glucose level comparable to standard drug pioglitazone. Compound 5e exhibited potent PPAR-gamma transactivation of 48.72% in comparison to pioglitazone (62.48%). All the molecules showed good glide score against the PPAR-gamma target in molecular docking study. PPAR-gamma gene expression was significantly increased by compound 5e (2.56-fold) in comparison to standard drug pioglitazone. Compounds 5e and 5c did not cause any damage to the liver and may be considered as promising candidates for the development of new antidiabetic agents. (C) 2014 Elsevier Ltd. All rights reserved.