(R)-1-O-octadecyl-3-(p-toluenesulfonyl)-glycerol | 83526-55-0

• 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: (R)-1-O-octadecyl-3-(p-toluenesulfonyl)-glycerol
• 英文别名: (R)-1-O-octadecyl-3-(p-toluenesulfonyl)glycerol；1-O-Octadecyl-3-O-p-toluolsulfonyl-sn-glycerin；[(2R)-2-hydroxy-3-octadecoxypropyl] 4-methylbenzenesulfonate
• CAS: 83526-55-0
• 化学式: C₂₈H₅₀O₅S
• 分子量: 498.768
• InChiKey: ONZIXUIFJLCXEJ-HHHXNRCGSA-N

物化性质

• 熔点：
  66-68 °C
• 沸点：
  606.2±50.0 °C(Predicted)
• 密度：
  1.021±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  34
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-1-O-octadecyl-3-(p-toluenesulfonyl)-glycerol 在 lithium aluminium tetrahydride 、 三氟甲磺酸 作用下， 以 1,4-二氧六环 、 乙醚 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 生成 1-O-octadecyl-2-O-benzyl-sn-glycerol
  参考文献：
  名称：

  Synthesis and Biological Activity of Anticancer Ether Lipids That Are Specifically Released by Phospholipase A₂ in Tumor Tissue

  摘要：

  The clinical use of anticancer lipids is severely limited by their ability to cause lysis of red blood cells prohibiting intravenous injection. Novel delivery systems are therefore required in order to develop anticancer ether lipids (AELs) into clinically useful anticancer drugs. In a recent article (J. Med. Chem. 2004, 4 7, 1694) we showed that it is possible to construct liposome systems composed of masked AELs that are activated by secretory phospholipase A(2) in cancerous tissue. We present here the synthesis of six AELs and evaluate the biological activity of these bioactive lipids. The synthesized AEL 1-6 were tested against three different cancer cell lines. It was found that the stereochemistry of the glycerol headgroup in AEL-2 and 3 has a dramatic effect on the cytotoxicity of the lipids. AEL 1-4 were furthermore evaluated for their ability to prevent phosphorylation of the apoptosis regulating kinase Akt, and a correlation was found between their cytotoxic activity and their ability to inhibit Akt phosphorylation.

  DOI：

  10.1021/jm049006f
• 作为产物：
  描述：

  3-O-Octadecyl-1,2-di-O-p-toluolsulfonyl-sn-glycerin 在 吡啶 、 氢氧化钾 作用下， 以 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 (R)-1-O-octadecyl-3-(p-toluenesulfonyl)-glycerol
  参考文献：
  名称：

  甘油醚磷脂的合成第1部分1 - O-十八烷基-2- O-乙酰基-sn-甘油-3-磷酸胆碱1（“血小板活化因子”），对映异构体和一些类似化合物的生产† ‡

  摘要：

  甘油醚磷脂的合成，第一次通讯，对映体和一些类似化合物的1- O-十八烷基-2- O-乙酰基-sn-甘油-3-磷酸胆碱（“血小板活化因子”）的制备

  DOI：

  10.1002/hlca.19820650339

文献信息

• Conformationally Restricted Analogs of Platelet-Activating Factor (PAF)
  作者：Paul Hadváry、Thomas Weller

  DOI：10.1002/hlca.19860690814

  日期：1986.12.10

  19, 22–25, and phosphoramidates 27–32 is described. The effects of these conformationally restricted platelet-activating factor analogs on rabbit platelet aggregation are briefly discussed. The 2-oxo-1,3,2-dioxaphosphorinanes 19, 25, and 30 were found to be equally potent platelet-activating factor antagonists as the known thiazolium salt 33.

  描述了五元环状磷酸二酰胺酸衍生物10和11的合成，以及六元环状磷酸酯18、19、22-25和氨基磷酸酯27-32的制备。简要讨论了这些构象受限的血小板活化因子类似物对兔血小板聚集的影响。的2-氧代-1,3,2-dioxaphosphorinanes 19,25，和30被认为是同等有效的血小板活化因子拮抗剂作为已知噻唑鎓盐33。
• [EN] PHOSPHOLIPID COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS PHOSPHOLIPIDIQUES ET LEURS UTILISATIONS
  申请人：GILEAD SCIENCES INC

  公开号：WO2022081973A1

  公开（公告）日：2022-04-21

  Compounds and methods of using said compounds, alone or in combination with additional agents, and pharmaceutical compositions of said compounds for the treatment of viral infections are disclosed.

  本文披露了用于治疗病毒感染的化合物及其使用方法，可以单独使用或与其他药物联合使用，并且还包括该化合物的药物组合物。
• Synthesis and Biophysical Characterization of Chlorambucil Anticancer Ether Lipid Prodrugs
  作者：Palle J. Pedersen、Mikkel S. Christensen、Tristan Ruysschaert、Lars Linderoth、Thomas L. Andresen、Fredrik Melander、Ole G. Mouritsen、Robert Madsen、Mads H. Clausen

  DOI：10.1021/jm900091h

  日期：2009.5.28

  The synthesis and biophysical characterization of four prodrug ether phospholipid conjugates are described. The lipids are prepared from the anticancer drug chlorambucil and have C16 and C18 ether chains with phosphatidylcholine or phosphatidylglycerol headgroups. All four prodrugs have the ability to form unilamellar liposomes (86-125 nm) and are hydrolyzed by phospholipase A(2), resulting in chlorambucil release. Liposomal formulations of prodrug lipids displayed cytotoxicity toward HT-29, MT-3, and ES-2 cancer cell lines in the presence of phospholipase A(2), with IC50 values in the 8-36 mu M range.
• Synthesis and Biological Activity of Anticancer Ether Lipids That Are Specifically Released by Phospholipase A₂ in Tumor Tissue
  作者：Thomas L. Andresen、Simon S. Jensen、Robert Madsen、Kent Jørgensen

  DOI：10.1021/jm049006f

  日期：2005.11.1

  The clinical use of anticancer lipids is severely limited by their ability to cause lysis of red blood cells prohibiting intravenous injection. Novel delivery systems are therefore required in order to develop anticancer ether lipids (AELs) into clinically useful anticancer drugs. In a recent article (J. Med. Chem. 2004, 4 7, 1694) we showed that it is possible to construct liposome systems composed of masked AELs that are activated by secretory phospholipase A(2) in cancerous tissue. We present here the synthesis of six AELs and evaluate the biological activity of these bioactive lipids. The synthesized AEL 1-6 were tested against three different cancer cell lines. It was found that the stereochemistry of the glycerol headgroup in AEL-2 and 3 has a dramatic effect on the cytotoxicity of the lipids. AEL 1-4 were furthermore evaluated for their ability to prevent phosphorylation of the apoptosis regulating kinase Akt, and a correlation was found between their cytotoxic activity and their ability to inhibit Akt phosphorylation.
• Synthese von Glyceryl�therphosphatiden 1. Mitteilung Herstellung von 1-O-Octadecyl-2-O-acetyl-sn-glyceryl-3-phosphorylcholin1 (?Platelet Activating Factor?), des Enantiomeren sowie einiger analoger Verbindungen
  作者：Georges Hirth、Richard Barner

  DOI：10.1002/hlca.19820650339

  日期：1982.5.5

  Synthesis of Glyceryletherphosphatides, 1st Communication, Preparation of 1-O-Octadecyl-2-O-acetyl-sn-glyceryl-3-phosphorylcholine (‘Platelet Activating Factor’), of its Enantiomer and of Some Analogous Compounds

  甘油醚磷脂的合成，第一次通讯，对映体和一些类似化合物的1- O-十八烷基-2- O-乙酰基-sn-甘油-3-磷酸胆碱（“血小板活化因子”）的制备