8-bromo-1-phenyl-1H-benzo[f]chromen-3(2H)-one | 1012319-46-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 8-bromo-1-phenyl-1H-benzo[f]chromen-3(2H)-one
• 英文别名: 8-Bromo-1-phenyl-1,2-dihydrobenzo[f]chromen-3-one
• CAS: 1012319-46-8
• 化学式: C₁₉H₁₃BrO₂
• 分子量: 353.215
• InChiKey: MJBSTCRRPXSAHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-bromo-1-phenyl-1H-benzo[f]chromen-3(2H)-one 、 氰化锌 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到3-Oxo-1-phenyl-1,2-dihydrobenzo[f]chromene-8-carbonitrile
  参考文献：
  名称：

  Structure–Activity Studies on Splitomicin Derivatives as Sirtuin Inhibitors and Computational Prediction of Binding Mode

  摘要：

  NAD(+)-dependent histone deacetylases (sirtuins) are enzymes that cleave acetyl groups from lysines in histones and other proteins. Potent selective sirtuin inhibitors are interesting tools for the investigation of the biological functions of those enzymes and may be future drugs for the treatment of cancer. Splitomicin was among the first two inhibitors that were discovered for yeast sirtuins but showed rather weak inhibition on human enzymes. We present detailed structure-activity relationships on splitomicin derivatives and their inhibition of recombinant Sirt2. To rationalize our experimental results, ligand docking followed by molecular mechanics Poisson - Boltzmann/surface area (MM-PBSA) calculations were carried out. These analyses suggested a molecular basis for the interaction of the beta-phenylsplitomicins with human Sirt2. Protein-based virtual screening resulted in the identification of a novel Sirt2 inhibitor chemotype. Selected inhibitors showed antiproliferative properties and tubulin hyperacetylation in MCF7 breast cancer cells and are promising candidates for further optimization as potential anticancer drugs.

  DOI：

  10.1021/jm700972e
• 作为产物：
  描述：

  (E)-3-Phenyl-acrylic acid 6-bromo-naphthalen-2-yl ester 在 potassium tert-butylate 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以82%的产率得到8-bromo-1-phenyl-1H-benzo[f]chromen-3(2H)-one
  参考文献：
  名称：

  N-杂环卡宾/钾离子协同催化α，β-不饱和酰基偶氮的苯甲酰化反应

  摘要：

  开发了α，β-不饱和酰基的催化苯基化反应。N-杂环卡宾和钾离子的结合可协同催化α，β-不饱和酰基zo与酚盐的环化，酚盐直接由α，β-不饱和酚盐产生。机理研究表明，钾离子在该反应中起着至关重要的作用。

  DOI：

  10.1002/ejoc.201600838