N-((2S,3S,5S)-11,11-difluoro-3,5-dihydroxyoctadecan-2-yl)formamide | 1372769-45-3

• 分子结构分类: 有机化合物
• 英文名称: N-((2S,3S,5S)-11,11-difluoro-3,5-dihydroxyoctadecan-2-yl)formamide
• CAS: 1372769-45-3
• 化学式: C₁₉H₃₇F₂NO₃
• 分子量: 365.504
• InChiKey: GWNBBQJAYKGGAP-BZSNNMDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  25.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  69.56
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-((2S,3S,5S)-11,11-difluoro-3,5-dihydroxyoctadecan-2-yl)formamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以31%的产率得到(2S,3S,5S)-11,11-difluoro-2-(methylamino)octadecane-3,5-diol
  参考文献：
  名称：

  Sphingolipid Analogues Inhibit Development of Malaria Parasites

  摘要：

  Plasmodium-infected erythrocytes have been shown to employ sphingolipids from both endogenous metabolism as well as existing host pools. Therapeutic agents that limit these supplies have thus emerged as intriguing, mechanistically distinct putative targets for the treatment of malaria infections. In an initial screen of our library of sphingolipid pathway modulators for efficacy against two strains of the predominant human malaria species Plasmodium falciparum and Plasmodium knowlesi, a series of orally available, 1-deoxysphingoid bases were found to possess promising in vitro antimalarial activity. To better understand the structural requirements that are necessary for this observed activity, a second series of modified analogues were prepared and evaluated. Initial pharmacokinetic assessments of key analogues were investigated to evaluate plasma and red blood cell concentrations in vivo.

  DOI：

  10.1021/ml2002136
• 作为产物：
  描述：

  (2S,5S)-2-(dibenzylamino)-9,9-difluoro-5-hydroxyoctadecan-3-one 在 sodium tetrahydroborate 、 氢气 、 palladium(II) hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， -20.0~20.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 生成 N-((2S,3S,5S)-11,11-difluoro-3,5-dihydroxyoctadecan-2-yl)formamide
  参考文献：
  名称：

  Sphingolipid Analogues Inhibit Development of Malaria Parasites

  摘要：

  Plasmodium-infected erythrocytes have been shown to employ sphingolipids from both endogenous metabolism as well as existing host pools. Therapeutic agents that limit these supplies have thus emerged as intriguing, mechanistically distinct putative targets for the treatment of malaria infections. In an initial screen of our library of sphingolipid pathway modulators for efficacy against two strains of the predominant human malaria species Plasmodium falciparum and Plasmodium knowlesi, a series of orally available, 1-deoxysphingoid bases were found to possess promising in vitro antimalarial activity. To better understand the structural requirements that are necessary for this observed activity, a second series of modified analogues were prepared and evaluated. Initial pharmacokinetic assessments of key analogues were investigated to evaluate plasma and red blood cell concentrations in vivo.

  DOI：

  10.1021/ml2002136