isobutyl 3-[3-(2,5-dioxo-3,4-dimethoxy-6-methylphenyl)propyloxymethylene]benzenesulfonate | 1429767-52-1

• 分子结构分类: 有机化合物
• 英文名称: isobutyl 3-[3-(2,5-dioxo-3,4-dimethoxy-6-methylphenyl)propyloxymethylene]benzenesulfonate
• 英文别名: 2-Methylpropyl 3-[3-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)propoxymethyl]benzenesulfonate
• CAS: 1429767-52-1
• 化学式: C₂₃H₃₀O₈S
• 分子量: 466.552
• InChiKey: AAHFEPPRXGFOBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  isobutyl 3-[3-(2,5-dioxo-3,4-dimethoxy-6-methylphenyl)propyloxymethylene]benzenesulfonate 在 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以51%的产率得到3-[3-(4,5-Dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)propoxymethyl]benzenesulfonic acid
  参考文献：
  名称：

  Anti-Leukemic Activity of Ubiquinone-Based Compounds Targeting Trans-plasma Membrane Electron Transport

  摘要：

  Trans-plasma membrane electron transport (tPMET) is a ubiquinone-dependent cell survival pathway for maintaining intracellular redox homeostasis in rapidly dividing cells. To target this pathway, fifteen ubiquinone-based compounds were designed and synthesized to position at the plasma membrane and disrupt tPMET. We established that quaternary ammonium salt moieties carrying highly hindered, positive electronic charges located to the plasma membrane. A ten-carbon chain linked to these moieties was effective at positioning the redox-active ubiquinone-like function within the lipid bilayer to disrupt tPMET in human leukemic cells (IC50 9 +/- 1 mu M). TPMET inhibition alone was not sufficient to induce significant cell death, but positively charged compounds could also enter the cell and disrupt intracellular redox balance, distinct from their effects on mitochondrial electron transport. The synergistic effect of tPMET inhibition plus intracellular redox disruption gave strong antiproliferative activity (IC50 2 +/- 0.2 mu M). Positively charged ubiquinone-based compounds inhibit human leukemic cell growth.

  DOI：

  10.1021/jm301585z
• 作为产物：
  描述：

  isobutyl 3-[3-(2,5-bis(benzyloxy)-3,4-dimethoxy-6-methylphenyl)propyloxymethylene]benzenesulfonate 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以62%的产率得到isobutyl 3-[3-(2,5-dioxo-3,4-dimethoxy-6-methylphenyl)propyloxymethylene]benzenesulfonate
  参考文献：
  名称：

  Anti-Leukemic Activity of Ubiquinone-Based Compounds Targeting Trans-plasma Membrane Electron Transport

  摘要：

  Trans-plasma membrane electron transport (tPMET) is a ubiquinone-dependent cell survival pathway for maintaining intracellular redox homeostasis in rapidly dividing cells. To target this pathway, fifteen ubiquinone-based compounds were designed and synthesized to position at the plasma membrane and disrupt tPMET. We established that quaternary ammonium salt moieties carrying highly hindered, positive electronic charges located to the plasma membrane. A ten-carbon chain linked to these moieties was effective at positioning the redox-active ubiquinone-like function within the lipid bilayer to disrupt tPMET in human leukemic cells (IC50 9 +/- 1 mu M). TPMET inhibition alone was not sufficient to induce significant cell death, but positively charged compounds could also enter the cell and disrupt intracellular redox balance, distinct from their effects on mitochondrial electron transport. The synergistic effect of tPMET inhibition plus intracellular redox disruption gave strong antiproliferative activity (IC50 2 +/- 0.2 mu M). Positively charged ubiquinone-based compounds inhibit human leukemic cell growth.

  DOI：

  10.1021/jm301585z