(2S,5S)-2-(dibenzylamino)-9,9-difluoro-5-hydroxyoctadecan-3-one | 1352303-24-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,5S)-2-(dibenzylamino)-9,9-difluoro-5-hydroxyoctadecan-3-one
• CAS: 1352303-24-2
• 化学式: C₃₂H₄₇F₂NO₂
• 分子量: 515.727
• InChiKey: IRDCYWKKYNDLBN-FIBWVYCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  37
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  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 为溶剂， -20.0~20.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 (2S,3S,5S)-2-amino-11,11-difluorooctadecane-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：

  1-(tetrahydro-2H-pyran-2-yloxy)tetradecan-7-ol 在 二甲基十二/十四烷基叔胺 、 (chlorobis((2S,3R)-3,6,6-trimethylbicyclo[3.1.1]heptan-2-yl)borane) 、 对甲苯磺酸 、 pyridinium chlorochromate 、 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 (2S,5S)-2-(dibenzylamino)-9,9-difluoro-5-hydroxyoctadecan-3-one
  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

文献信息

• Sphingosine Analogs, Compositions, and Methods Related Thereto
  申请人：Emory University

  公开号：US20140309275A1

  公开（公告）日：2014-10-16

  The disclosure relates to compounds, pharmaceutical compositions, and methods of treating or preventing disease. In certain embodiments, the disclosure relates to methods of treating an infection or cancer comprising administering a pharmaceutical composition disclosed herein to a subject in need thereof. In a typical embodiment, one administers a pharmaceutical composition comprising sphingosine or a sphingosine analog to a subject at risk for, exhibiting symptoms of or diagnosed with a malaria infection.

  该披露涉及化合物、药物组合物以及治疗或预防疾病的方法。在某些实施例中，该披露涉及治疗感染或癌症的方法，包括向需要的受试者施用本文披露的药物组合物。在典型实施例中，人们向患有疟疾感染风险、表现症状或被诊断患有疟疾感染的受试者施用含有鞘氨醇或鞘氨醇类似物的药物组合物。
• [EN] SPHINGOSINE ANALOGS, COMPOSITIONS, AND METHODS RELATED THERETO<br/>[FR] ANALOGUES DE SPHINGOSINE, COMPOSITIONS ET PROCÉDÉS AFFÉRENTS
  申请人：UNIV EMORY

  公开号：WO2013049280A2

  公开（公告）日：2013-04-04

  The disclosure relates to compounds, pharmaceutical compositions, and methods of treating or preventing disease. In certain embodiments, the disclosure relates to methods of treating an infection or cancer comprising administering a pharmaceutical composition disclosed herein to a subject in need thereof. In a typical embodiment, one administers a pharmaceutical composition comprising sphingosine or a sphingosine analog to a subject at risk for, exhibiting symptoms of, or diagnosed with a malaria infection.