3,4-dimethoxy-6-methyl-2,5-bis(phenylmethoxy)benzenedecanol | 1360862-57-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3,4-dimethoxy-6-methyl-2,5-bis(phenylmethoxy)benzenedecanol
• CAS: 1360862-57-2
• 化学式: C₃₃H₄₄O₅
• 分子量: 520.709
• InChiKey: LMJUNECGSMYTMC-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  3,4-dimethoxy-6-methyl-2,5-bis(phenylmethoxy)benzenedecanol 在 5%-palladium/activated carbon 、 氢气 、 sodium hydride 、 sodium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 16.5h， 生成 3-[10-(4,5-Dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)decoxymethyl]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