3-(cyclohexanecarbonyl)-4-hydroxy-5,6-dimethoxy-1H-pyridin-2-one | 1222884-66-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(cyclohexanecarbonyl)-4-hydroxy-5,6-dimethoxy-1H-pyridin-2-one
• CAS: 1222884-66-3
• 化学式: C₁₄H₁₉NO₅
• 分子量: 281.309
• InChiKey: QLRNWLJYGXFRNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 生成 3-(cyclohexanecarbonyl)-4-hydroxy-5,6-dimethoxy-1H-pyridin-2-one
  参考文献：
  名称：

  Synthetic atpenin analogs: Potent mitochondrial inhibitors of mammalian and fungal succinate-ubiquinone oxidoreductase

  摘要：

  Atpenins and harzianopyridone represent a unique class of penta-substituted pyridine-based natural products that are potent inhibitors of complex II (succinate-ubiquinone oxidoreductase) in the mitochondrial respiratory chain. These compounds block electron transfer in oxidative phosphorylation by inhibiting oxidation of succinate to fumarate and the coupled reduction of ubiquinone to ubiquinol. From our investigations of complex II inhibitors as potential agricultural fungicides, we report here on the synthesis and complex II inhibition for a series of synthetic atpenin analogs against both mammalian and fungal forms of the enzyme. Synthetic atpenin 2e provided optimum mammalian and fungal inhibition with slightly higher potency than natural occurring atpenin A5. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.066

文献信息

• Synthetic atpenin analogs: Potent mitochondrial inhibitors of mammalian and fungal succinate-ubiquinone oxidoreductase
  作者：Thomas P. Selby、Kenneth A. Hughes、James J. Rauh、Wayne S. Hanna

  DOI：10.1016/j.bmcl.2010.01.066

  日期：2010.3

  Atpenins and harzianopyridone represent a unique class of penta-substituted pyridine-based natural products that are potent inhibitors of complex II (succinate-ubiquinone oxidoreductase) in the mitochondrial respiratory chain. These compounds block electron transfer in oxidative phosphorylation by inhibiting oxidation of succinate to fumarate and the coupled reduction of ubiquinone to ubiquinol. From our investigations of complex II inhibitors as potential agricultural fungicides, we report here on the synthesis and complex II inhibition for a series of synthetic atpenin analogs against both mammalian and fungal forms of the enzyme. Synthetic atpenin 2e provided optimum mammalian and fungal inhibition with slightly higher potency than natural occurring atpenin A5. (C) 2010 Elsevier Ltd. All rights reserved.