(Z)-5-(6-methyl-4-oxo-4H-chromen-3-ylmethylene)-2-thioxoimidazolidine-4-one

• 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: (Z)-5-(6-methyl-4-oxo-4H-chromen-3-ylmethylene)-2-thioxoimidazolidine-4-one
• 英文别名: (Z)-5-((6-methyl-4-oxo-4H-chromen-3-yl)methylene)-2-thioxoimidazolidin-4-one；(5Z)-5-[(6-methyl-4-oxochromen-3-yl)methylidene]-2-sulfanylideneimidazolidin-4-one
• 化学式: C₁₄H₁₀N₂O₃S
• 分子量: 286.311
• InChiKey: PCFGEVGNTBWOSO-YHYXMXQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  99.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-5-(6-methyl-4-oxo-4H-chromen-3-ylmethylene)-2-thioxoimidazolidine-4-one 、 碘乙烷 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以65.5%的产率得到(Z)-3-ethyl-2-ethylsulfanyl-5-(6-methyl-4-oxo-4H-chromen-3-ylmethylene)-3,5-dihydroimidazol-4-one
  参考文献：
  名称：

  Synthesis and antidiabetic activity of 2,4-thiazolidindione, imidazolidinedione and 2-thioxo-imidazolidine-4-one derivatives bearing 6-methyl chromonyl pharmacophore

  摘要：

  Numerous compounds have been prepared in order to improve the pharmacological profile of insulinotropic activities. In the present paper, we report the synthesis and the in vitro insulin releasing activity of the 6-methyl-chromonyl-2,4-thiazolidinediones (IIIa-c, IVa-c, Va-c). Compounds IIIb, IIIc, IVa-c, Va and Vc (at lower concentration; 0.001 mg/mL) were able to increase insulin release in the presence of 5.6 mmol/L glucose. In this series, the most potent compound is IVa having methyl group at N3 position of TZD ring.

  DOI：

  10.3109/14756366.2012.723207
• 作为产物：
  描述：

  6-甲基-4-氧-4H-1-苯并吡喃-3-甲醛 、 2-硫代乙内酰脲 在 sodium acetate 、 溶剂黄146 作用下， 反应 5.0h， 以88.8%的产率得到(Z)-5-(6-methyl-4-oxo-4H-chromen-3-ylmethylene)-2-thioxoimidazolidine-4-one
  参考文献：
  名称：

  Synthesis and antidiabetic activity of 2,4-thiazolidindione, imidazolidinedione and 2-thioxo-imidazolidine-4-one derivatives bearing 6-methyl chromonyl pharmacophore

  摘要：

  Numerous compounds have been prepared in order to improve the pharmacological profile of insulinotropic activities. In the present paper, we report the synthesis and the in vitro insulin releasing activity of the 6-methyl-chromonyl-2,4-thiazolidinediones (IIIa-c, IVa-c, Va-c). Compounds IIIb, IIIc, IVa-c, Va and Vc (at lower concentration; 0.001 mg/mL) were able to increase insulin release in the presence of 5.6 mmol/L glucose. In this series, the most potent compound is IVa having methyl group at N3 position of TZD ring.

  DOI：

  10.3109/14756366.2012.723207

文献信息

• POLYAKOV V. K.; SHEVTSOVA R. G.; TSUKERMAN S. V., UKR. XIM. ZH., 1981, 47, HO 1, 85-87
  作者：POLYAKOV V. K.、 SHEVTSOVA R. G.、 TSUKERMAN S. V.

  DOI：——

  日期：——