5-[(3-Hydroxyphenyl)methylidene]imidazolidine-2,4-dione | 91426-39-0

• 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: 5-[(3-Hydroxyphenyl)methylidene]imidazolidine-2,4-dione
• CAS: 91426-39-0
• 化学式: C₁₀H₈N₂O₃
• 分子量: 204.185
• InChiKey: HZAHUPKFCIYWHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  300°C dec.
• 密度：
  1.458±0.06 g/cm3(Predicted)
• 溶解度：
  DMF、二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[(3-Hydroxyphenyl)methylidene]imidazolidine-2,4-dione 在 水 、 sodium hydroxide 作用下， 反应 3.0h， 以0.7 g的产率得到2-hydroxy-3-(3-hydroxyphenyl)acrylic acid
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of substrate-competitive inhibitors of C-terminal Binding Protein (CtBP)

  摘要：

  C-terminal Binding Protein (CtBP) is a transcriptional co-regulator that downregulates the expression of many tumor-suppressor genes. Utilizing a crystal structure of CtBP with its substrate 4-methylthio-2-oxobutyric acid (MTOB) and NAD(+) as a guide, we have designed, synthesized, and tested a series of small molecule inhibitors of CtBP. From our first round of compounds, we identified 2-(hydroxyimino)-3-phenylpropanoic acid as a potent CtBP inhibitor (IC50 = 0.24 mu M). A structure-activity relationship study of this compound further identified the 4-chloro- (IC50 = 0.18 mu M) and 3-chloro- (IC50 = 0.17 mu M) analogues as additional potent CtBP inhibitors. Evaluation of the hydroxyimine analogues in a short-term cell growth/viability assay showed that the 4-chloro- and 3-chloro-analogues are 2-fold and 4-fold more potent, respectively, than the MTOB control. A functional cellular assay using a CtBP-specific transcriptional readout revealed that the 4-chloro- and 3-chloro-hydroxyimine analogues were able to block CtBP transcriptional repression activity. This data suggests that substrate-competitive inhibition of CtBP dehydrogenase activity is a potential mechanism to reactivate tumor-suppressor gene expression as a therapeutic strategy for cancer. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.04.037
• 作为产物：
  描述：

  海因 、 间羟基苯甲醛 在 C.I.酸性橙108 作用下， 以 乙醇 、 水 为溶剂， 生成 5-[(3-Hydroxyphenyl)methylidene]imidazolidine-2,4-dione
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of substrate-competitive inhibitors of C-terminal Binding Protein (CtBP)

  摘要：

  C-terminal Binding Protein (CtBP) is a transcriptional co-regulator that downregulates the expression of many tumor-suppressor genes. Utilizing a crystal structure of CtBP with its substrate 4-methylthio-2-oxobutyric acid (MTOB) and NAD(+) as a guide, we have designed, synthesized, and tested a series of small molecule inhibitors of CtBP. From our first round of compounds, we identified 2-(hydroxyimino)-3-phenylpropanoic acid as a potent CtBP inhibitor (IC50 = 0.24 mu M). A structure-activity relationship study of this compound further identified the 4-chloro- (IC50 = 0.18 mu M) and 3-chloro- (IC50 = 0.17 mu M) analogues as additional potent CtBP inhibitors. Evaluation of the hydroxyimine analogues in a short-term cell growth/viability assay showed that the 4-chloro- and 3-chloro-analogues are 2-fold and 4-fold more potent, respectively, than the MTOB control. A functional cellular assay using a CtBP-specific transcriptional readout revealed that the 4-chloro- and 3-chloro-hydroxyimine analogues were able to block CtBP transcriptional repression activity. This data suggests that substrate-competitive inhibition of CtBP dehydrogenase activity is a potential mechanism to reactivate tumor-suppressor gene expression as a therapeutic strategy for cancer. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.04.037