1-O-octadecyl-2-O-benzyl-sn-glycerol | 80707-93-3

• 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: 1-O-octadecyl-2-O-benzyl-sn-glycerol
• 英文别名: 1-Propanol, 3-(octadecyloxy)-2-(phenylmethoxy)-, (S)-；(2S)-3-octadecoxy-2-phenylmethoxypropan-1-ol
• CAS: 80707-93-3
• 化学式: C₂₈H₅₀O₃
• 分子量: 434.703
• InChiKey: AVIFKOIVNVRTPE-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  31
• 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：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-O-octadecyl-2-O-benzyl-sn-glycerol 在 palladium on activated charcoal 盐酸 、 叔丁基过氧化氢 、 氢气 、 胸苷酸 、 三甲胺 作用下， 以 甲醇 、 癸烷 、 二氯甲烷 、 乙酸乙酯 、 异丙醇 、 乙腈 为溶剂， 反应 10.5h， 生成 1-O-octadecyl-2-hydroxy-sn-glycero-3-phospho-(S)-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：

  硬脂醇 在 lithium aluminium tetrahydride 、 三氟甲磺酸 、 三氟化硼乙醚 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 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

文献信息

• [EN] ANTIVIRAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIVIRAUX
  申请人：GILEAD SCIENCES INC

  公开号：WO2021167882A1

  公开（公告）日：2021-08-26

  The present disclosure provides compounds for treating a variety of diseases, such as respiratory syncytial virus (RSV), HRV, hMPV, ebola, Zika, West Nile, Dengue, and HCV.

  本公开提供了用于治疗各种疾病的化合物，如呼吸道合胞病毒（RSV）、人 rhinovirus（HRV）、人类副流感病毒（hMPV）、埃博拉病毒、寨卡病毒、西尼罗河病毒、登革热病毒和丙型肝炎病毒（HCV）。
• Comparison of the Antiviral Activities of Alkoxyalkyl and Alkyl Esters of Cidofovir against Human and Murine Cytomegalovirus Replication In Vitro
  作者：William B. Wan、James R. Beadle、Caroll Hartline、Earl R. Kern、Stephanie L. Ciesla、Nadejda Valiaeva、Karl Y. Hostetler

  DOI：10.1128/aac.49.2.656-662.2005

  日期：2005.2

  Alkoxyalkyl esters of cidofovir (CDV) have substantially greater antiviral activity and selectivity than unmodified CDV against herpesviruses and orthopoxviruses in vitro. Enhancement of antiviral activity was also noted when cyclic CDV was esterified with alkoxyalkanols. In vitro antiviral activity of the most active analogs against human cytomegalovirus (HCMV) and orthopoxviruses was increased relative to CDV up to 1,000- or 200-fold, respectively. Alkyl chain length and linker structure are important potential modifiers of antiviral activity and selectivity. In this study, we synthesized a series of alkoxyalkyl esters of CDV or cyclic CDV with alkyl chains from 8 to 24 atoms and having linker moieties of glycerol, propanediol, and ethanediol. We also synthesized alkyl esters of CDV which lack the linker to determine if the alkoxyalkyl linker moiety is required for activity. The new compounds were evaluated in vitro against HCMV and murine CMV (MCMV). CDV or cyclic CDV analogs both with and without linker moieties were highly active against HCMV and MCMV, and their activities were strongly dependent on chain length. The most active compounds had 20 atoms esterified to the phosphonate of CDV. Both alkoxypropyl and alkyl esters of CDV provided enhanced antiviral activities against CMV in vitro. Thus, the oxypropyl linker moiety is not required for enhanced activity. CDV analogs having alkyl ethers linked to glycerol or ethanediol linker groups also demonstrated increased activity against CMV.

  摘要 西多福韦（CDV）的烷氧基烷基酯在体外对疱疹病毒和正疱疹病毒的抗病毒活性和选择性大大高于未改性的 CDV。当环状 CDV 与烷氧基烷醇酯化时，抗病毒活性也会增强。与 CDV 相比，最活跃的类似物对人类巨细胞病毒（HCMV）和正痘病毒的体外抗病毒活性分别提高了 1000 倍和 200 倍。烷基链长度和连接体结构是抗病毒活性和选择性的重要潜在调节剂。在这项研究中，我们合成了一系列 CDV 烷氧基烷基酯或环 CDV 烷氧基烷基酯，其烷基链长度为 8 至 24 个原子，链接分子为甘油、丙二醇和乙二醇。我们还合成了缺少连接基的 CDV 烷基酯，以确定烷氧基烷基连接基是否为活性所必需。我们对这些新化合物进行了抗 HCMV 和小鼠 CMV (MCMV) 的体外评估。含有或不含连接基的 CDV 或环状 CDV 类似物对 HCMV 和 MCMV 都具有很高的活性，而且它们的活性与链长密切相关。活性最强的化合物有 20 个原子酯化到 CDV 的膦酸盐上。CDV 的烷氧基丙基酯和烷基酯都能在体外增强对 CMV 的抗病毒活性。因此，增强活性并不需要氧丙基连接分子。烷基醚与甘油或乙二醇连接基连接的 CDV 类似物也显示出更强的抗 CMV 活性。
• Glycerin derivatives and inhibition of blood PAF
  申请人：Hoffman-La Roche Inc.

  公开号：US04731373A1

  公开（公告）日：1988-03-15

  Glycerine derivatives of the formula ##STR1## wherein the residues R.sup.1, R.sup.2 and R.sup.3 have the significance given in the description, and their hydrates, which inhibit blood platelet activating factor (PAF), are descried.

  甘油衍生物的化学式为##STR1##，其中残基R.sup.1、R.sup.2和R.sup.3具有描述中给定的意义，以及它们的水合物，可以抑制血小板活化因子（PAF）。
• Method of use of 1-(alkyl for alkylcarbanoyl)-2-carbamoylglycerol
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04576933A1

  公开（公告）日：1986-03-18

  Glycerol derivatives, inclusive of salts thereof, of the formula ##STR1## wherein R.sup.1 is alkyl or alkylcarbamoyl containing 10 to 30 carbon atoms, R.sup.2 and R.sup.3 are independently hydrogen, C.sub.1-6 alkyl or, taken together with the adjacent nitrogen atom, form cyclic amino, and ##STR2## represents cyclic ammonio, and of the formula ##STR3## wherein R.sup.1 is as defined above, R.sup.2' and R.sup.3' are C.sub.1-6 alkyl or, taken together with the adjacent nitrogen atom, form cyclic amino and R.sup.4', R.sup.5' and R.sup.6' are independently hydrogen or C.sub.1-6 alkyl, are useful as antihypertensive agents.

  甘油衍生物，包括其盐，其化学式为##STR1##其中R.sup.1是含有10到30个碳原子的烷基或烷基氨基甲酰，R.sup.2和R.sup.3分别是氢、C.sub.1-6烷基或与相邻的氮原子结合形成环状氨基，而##STR2##表示环状铵离子，以及化学式##STR3##其中R.sup.1如上定义，R.sup.2'和R.sup.3'是C.sub.1-6烷基或与相邻的氮原子结合形成环状氨基，R.sup.4'、R.sup.5'和R.sup.6'分别是氢或C.sub.1-6烷基，可用作降压药。
• 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