3-(4-chlorobenzoyl)-4-hydroxy-5,6-dimethoxy-1H-pyridin-2-one | 1222884-72-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-chlorobenzoyl)-4-hydroxy-5,6-dimethoxy-1H-pyridin-2-one
• CAS: 1222884-72-1
• 化学式: C₁₄H₁₂ClNO₅
• 分子量: 309.706
• InChiKey: AKUBLUMIJSKTMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲基磺酰氯 、 3-(4-chlorobenzoyl)-4-hydroxy-5,6-dimethoxy-1H-pyridin-2-one 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以30%的产率得到[5-(4-Chlorobenzoyl)-2,3-dimethoxy-6-methylsulfonyloxypyridin-4-yl] methanesulfonate
  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
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以0.17 g的产率得到3-(4-chlorobenzoyl)-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

• ATPENINS
  申请人：ADELT Isabelle

  公开号：US20100168175A1

  公开（公告）日：2010-07-01

  The present invention relates to processes for preparing certain 2-pyridones and 2-pyridinols, to novel compounds of these two types and to their use as biologically active compounds, in particular for controlling harmful microorganisms in crop protection, in the medicinal field and in the protection of materials.

  本发明涉及制备特定2-吡啶酮和2-吡啶醇的过程，涉及这两种类型的新化合物以及它们作为生物活性化合物的用途，特别是用于控制农作物保护中的有害微生物，在医药领域和材料保护中。
• [DE] ATPENINE<br/>[EN] ATPENINS<br/>[FR] ATPÉNINE
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2010069495A1

  公开（公告）日：2010-06-24

  Die vorliegende Erfindung betrifft Verfahren zum Herstellen von bestimmten 2-Pyridonen und 2-Pyridinolen, neue Verbindungen dieser beiden Typen sowie deren Verwendung als biologisch aktive Verbindungen, insbesondere zur Bekämpfung von schädlichen Mikroorganismen im Pflanzenschutz, im medizinischen Bereich und im Materialschutz.
• 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.