(R)-2-[3-hydroxy-3-methylundecyl]-6-methoxy-3,5-dimethyl-4H-pyran-4-one | 1234334-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (R)-2-[3-hydroxy-3-methylundecyl]-6-methoxy-3,5-dimethyl-4H-pyran-4-one
• 英文别名: 2-[(3R)-3-hydroxy-3-methylundecyl]-6-methoxy-3,5-dimethylpyran-4-one
• CAS: 1234334-38-3
• 化学式: C₂₀H₃₄O₄
• 分子量: 338.488
• InChiKey: PLHADEKOUZFLFG-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-癸酮 在 吡啶 、 正丁基锂 、 AD-mix β 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 16.08h， 生成 (R)-2-[3-hydroxy-3-methylundecyl]-6-methoxy-3,5-dimethyl-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis and evaluation of verticipyrone analogues as mitochondrial complex I inhibitors

  摘要：

  Verticipyrone has recently been isolated from the culture broth of Verticillium sp. and shown to inhibit NADH fumarate reductase, as well as NADH oxidoreductase ( complex I) of the mitochondrial electron transport chain. In order to assess the structural elements in verticipyrone essential for complex I inhibitor, 15 structural analogues were prepared and analyzed for their effects on mitochondrial NADH oxidoreductase and NADH oxidase activities. Also measured were the abilities of several of the analogues to inhibit respiration as judged by a shift to glycolysis, and to inhibit the growth of several mammalian cell lines. The nature of the pyrone ring was shown to be important to potency of inhibition, as was the length and nature of substituents in the side chain of the analogues. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.070

文献信息

• Synthesis and evaluation of verticipyrone analogues as mitochondrial complex I inhibitors
  作者：Simon J. Leiris、Omar M. Khdour、Zachary J. Segerman、Krystal S. Tsosie、Jean-Charles Chapuis、Sidney M. Hecht

  DOI：10.1016/j.bmc.2010.03.070

  日期：2010.5

  Verticipyrone has recently been isolated from the culture broth of Verticillium sp. and shown to inhibit NADH fumarate reductase, as well as NADH oxidoreductase ( complex I) of the mitochondrial electron transport chain. In order to assess the structural elements in verticipyrone essential for complex I inhibitor, 15 structural analogues were prepared and analyzed for their effects on mitochondrial NADH oxidoreductase and NADH oxidase activities. Also measured were the abilities of several of the analogues to inhibit respiration as judged by a shift to glycolysis, and to inhibit the growth of several mammalian cell lines. The nature of the pyrone ring was shown to be important to potency of inhibition, as was the length and nature of substituents in the side chain of the analogues. (C) 2010 Elsevier Ltd. All rights reserved.