1-acetyl-1H-cinnolin-4-one | 93334-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-acetyl-1H-cinnolin-4-one
• 英文别名: 1-Acetyl-1H-cinnolin-4-on；1-Acetyl-4-cinnolon；1-Acetylcinnolin-4-one
• CAS: 93334-81-7
• 化学式: C₁₀H₈N₂O₂
• 分子量: 188.186
• InChiKey: KPOSKPNVQAAPSU-UHFFFAOYSA-N

物化性质

• 沸点：
  347.3±25.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-硝基苯基丙炔酸 在 乙酸酐 、 iron(II) sulfate 作用下， 生成 1-acetyl-1H-cinnolin-4-one
  参考文献：
  名称：

  131. Cinnolines。第三部分 里希特反应

  摘要：

  DOI：

  10.1039/jr9450000512

文献信息

• Cinnoline derivatives as human neutrophil elastase inhibitors
  作者：Maria Paola Giovannoni、Igor A. Schepetkin、Letizia Crocetti、Giovanna Ciciani、Agostino Cilibrizzi、Gabriella Guerrini、Andrei I. Khlebnikov、Mark T. Quinn、Claudia Vergelli

  DOI：10.3109/14756366.2015.1057718

  日期：2016.7.3

  Compounds that can effectively inhibit the proteolytic activity of human neutrophil elastase (HNE) represent promising therapeutics for treatment of inflammatory diseases. We present here the synthesis, structure-activity relationship analysis, and biological evaluation of a new series of HNE inhibitors with a cinnoline scaffold. These compounds exhibited HNE inhibitory activity but had lower potency compared to N-benzoylindazoles previously reported by us. On the other hand, they exhibited increased stability in aqueous solution. The most potent compound, 18a, had a good balance between HNE inhibitory activity (IC50 value = 56 nM) and chemical stability (t(1/2) = 114 min). Analysis of reaction kinetics revealed that these cinnoline derivatives were reversible competitive inhibitors of HNE. Furthermore, molecular docking studies of the active products into the HNE binding site revealed two types of HNE inhibitors: molecules with cinnolin-4(1H)-one scaffold, which were attacked by the HNE Ser195 hydroxyl group at the amido moiety, and cinnoline derivatives containing an ester function at C-4, which is the point of attack of Ser195.
• Keneford et al., Journal of the Chemical Society, 1948, p. 358,359
  作者：Keneford et al.

  DOI：——

  日期：——
• Bruce et al., Journal of the Chemical Society, 1964, p. 4044
  作者：Bruce et al.

  DOI：——

  日期：——