(2S,3S,5S)-2-amino-11,11-difluorooctadecane-3,5-diol | 1352303-03-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,3S,5S)-2-amino-11,11-difluorooctadecane-3,5-diol
• CAS: 1352303-03-7
• 化学式: C₁₈H₃₇F₂NO₂
• 分子量: 337.494
• InChiKey: RDYODIXCKUHTSH-ULQDDVLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,5S)-2-amino-11,11-difluorooctadecane-3,5-diol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (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：

  1-(tetrahydro-2H-pyran-2-yloxy)tetradecan-7-ol 在 sodium tetrahydroborate 、 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) 、 氢气 、 palladium(II) hydroxide 、 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， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 11.5h， 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

文献信息

• [EN] NUCLEOTIDE AND NUCLEOSIDE COMPOSITIONS AND USES RELATED THERETO<br/>[FR] COMPOSITIONS À BASE DE NUCLÉOTIDE ET DE NUCLÉOSIDE ET UTILISATIONS CORRESPONDANTES
  申请人：UNIV EMORY

  公开号：WO2015038596A1

  公开（公告）日：2015-03-19

  This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

  这份披露涉及到核苷酸和核苷类治疗组合物，用于治疗传染病、病毒感染和癌症，在这些组合物中，核苷酸或核苷的碱基至少含有一个硫醇、硫酮或硫醚。
• [EN] NUCLEOTIDE AND NUCLEOSIDE THERAPEUTICS COMPOSITIONS AND USES RELATED THERETO<br/>[FR] COMPOSITIONS THÉRAPEUTIQUES RENFERMANT DES NUCLÉOTIDES ET DES NUCLÉOSIDES ET UTILISATIONS ASSOCIÉES
  申请人：UNIV EMORY

  公开号：WO2016145142A1

  公开（公告）日：2016-09-15

  This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

  这份披露涉及到核苷酸和核苷类治疗组合物，用于治疗传染病、病毒感染和癌症，其中核苷酸或核苷的碱基至少含有一个硫醇、硫醌或硫醚。
• [EN] N4-HYDROXYCYTIDINE AND DERIVATIVES AND ANTI-VIRAL USES RELATED THERETO<br/>[FR] N4-HYDROXYCYTIDINE, SES DÉRIVÉS ET UTILISATIONS ANTI-VIRALES
  申请人：UNIV EMORY

  公开号：WO2016106050A1

  公开（公告）日：2016-06-30

  This disclosure relates to N4-hydroxycytidine derivatives, compositions, and methods related thereto. In certain embodiments, the disclosure relates to the treatment and prophylaxis of viral infections.

  这项披露涉及N4-羟基胞嘧啶衍生物、组合物以及相关方法。在某些实施方式中，该披露涉及治疗和预防病毒感染。
• [EN] N4-HYDROXYCYTIDINE AND DERIVATIVES AND ANTI-VIRAL USES RELATED THERETO<br/>[FR] N4-HYDROXYCYTIDINE ET DÉRIVÉS ET LEURS UTILISATIONS ANTI-VIRALES
  申请人：UNIV EMORY

  公开号：WO2017156380A1

  公开（公告）日：2017-09-14

  This disclosure relates to certain N4-hydroxycytidine derivatives, compositions, and methods related thereto. In certain embodiments, the disclosure relates to the treatment or prophylaxis of a Zika virus infection.

  这项披露涉及某些N4-羟基胞嘧啶衍生物，相关组合物和方法。在某些实施例中，该披露涉及治疗或预防寨卡病毒感染。
• 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。