N-(2-hydroxy-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)nicotinamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: N-(2-hydroxy-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)nicotinamide
• 化学式: C₁₅H₁₀N₂O₄
• 分子量: 282.255
• InChiKey: PWQKWMUCTFVGBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  96.36
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  水合茚三酮 、 烟酰胺 在 magnesium sulfate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以5%的产率得到N-(2-hydroxy-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)nicotinamide
  参考文献：
  名称：

  Inhibition of the HIF1α-p300 interaction by quinone- and indandione-mediated ejection of structural Zn(II)

  摘要：

  Protein-protein interactions between the hypoxia inducible factor (HIF) and the transcriptional coactivators p300/CBP are potential cancer targets due to their role in the hypoxic response. A natural product based screen led to the identification of indandione and benzoquinone derivatives that reduce the tight interaction between a HIF-1 alpha fragment and the CH1 domain of p300. The indandione derivatives were shown to fragment to give ninhydrin, which was identified as the active species. Both the naphthoquinones and ninhydrin were observed to induce Zn(II) ejection from p300 and the catalytic domain of the histone demethylase KDM4A. Together with previous reports on the effects of related compounds on HIF-1 alpha and other systems, the results suggest that care should be taken in interpreting biological results obtained with highly electrophilic/thiol modifying compounds. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.06.006

文献信息

• Inhibition of the HIF1α-p300 interaction by quinone- and indandione-mediated ejection of structural Zn(II)
  作者：Madura K.P. Jayatunga、Sam Thompson、Tawnya C. McKee、Mun Chiang Chan、Kelie M. Reece、Adam P. Hardy、Rok Sekirnik、Peter T. Seden、Kristina M. Cook、James B. McMahon、William D. Figg、Christopher J. Schofield、Andrew D. Hamilton

  DOI：10.1016/j.ejmech.2014.06.006

  日期：2015.4

  Protein-protein interactions between the hypoxia inducible factor (HIF) and the transcriptional coactivators p300/CBP are potential cancer targets due to their role in the hypoxic response. A natural product based screen led to the identification of indandione and benzoquinone derivatives that reduce the tight interaction between a HIF-1 alpha fragment and the CH1 domain of p300. The indandione derivatives were shown to fragment to give ninhydrin, which was identified as the active species. Both the naphthoquinones and ninhydrin were observed to induce Zn(II) ejection from p300 and the catalytic domain of the histone demethylase KDM4A. Together with previous reports on the effects of related compounds on HIF-1 alpha and other systems, the results suggest that care should be taken in interpreting biological results obtained with highly electrophilic/thiol modifying compounds. (C) 2014 Elsevier Masson SAS. All rights reserved.