rac-1,2-di-O-hexadecyl-3-O-(4-toluenesulfonyl)glycerol | 70077-48-4

• 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: rac-1,2-di-O-hexadecyl-3-O-(4-toluenesulfonyl)glycerol
• 英文别名: rac-1,2-dihexadecyl-3-tosylglycerol；α,β-Di-O-hexadecyl-α¹-O-tosyl glycerol；1,2-Di-O-hexadecylglycero-3-(p-toluensulfonsaeureester)；2,3-di-O-hexadecyl-1-glyceryl tosylate；1,2-di-0-(n-hexadecyl)-3-0-(p-tosyl)-glycerol；1,2-di-O-(n-hexadecyl)-3-O-(p-tosyl)-glycerol；1-tosyl-[2,3-dihexadecyl]-glycerine；2,3-Dihexadecoxypropyl 4-methylbenzenesulfonate
• CAS: 70077-48-4
• 化学式: C₄₂H₇₈O₅S
• 分子量: 695.144
• InChiKey: DTWBWWACYDQKAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.8
• 重原子数：
  48
• 可旋转键数：
  37
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  rac-1,2-di-O-hexadecyl-3-O-(4-toluenesulfonyl)glycerol 在 silver(I) acetate 、 二甲胺 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 48.0h， 生成 dl-[1,2-Di-O-hexadecyl-3-(dimethylamino)]propane
  参考文献：
  名称：

  Rueger; Kertscher; Nuhn, Pharmazie, 1980, vol. 35, # 1, p. 50 - 51

  摘要：

  DOI：
• 作为产物：
  描述：

  dl-α,β-Di-O-hexadecyl-O-benzylglycerol 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 52.0h， 生成 rac-1,2-di-O-hexadecyl-3-O-(4-toluenesulfonyl)glycerol
  参考文献：
  名称：

  Lipid-catalyzed transport of copper(II) through liquid membranes

  摘要：

  Six long-chained ligands were synthesized and examined for their ability to transport Cu(II) through a liquid membrane. The transport was proton-driven and capable of moving metal ions ''up-hill''. The time-dependence of the Cu(II) concentrations was determined for each carrier and for all three phases of the liquid membrane system. Thus, it was possible to follow the transfer of Cu(II) from the aqueous source phase to the organic layer and from the organic layer to the aqueous receiving phase. In addition, relative partitioning equilibria of Cu(III) between the organic layer and the aqueous phases were compared. It was found that all transport rates were kinetically controlled. Of the six carriers, only one was truly effective (the others experiencing difficulties releasing Cu(II) into the receiving phase). This one carrier displayed a remarkable activity exceeding that of LIX63 (a 'standard' in industrial extractions from copper ore). The activity was attributed to the carrier bearing polar hydroxyls at the ligand end of molecule, thereby enhancing the affinity for the organic/water interface where the rate-determining reactions take place. Studies were carried out varying the pH of the aqueous phases, the carrier concentration, and the nature of the organic layer.

  DOI：

  10.1021/jo00059a050

文献信息

• Di-O-n-alkyl glycerol derivatives as immune stimulants
  申请人：Pfizer Inc.

  公开号：US04173641A1

  公开（公告）日：1979-11-06

  Novel 1,2- and 1,3-(di-O-n-alkyl)glycerol derivatives and their pharmaceutically acceptable acid addition salts are useful as non-specific stimulants of cell-mediated immunity.

  小说1,2-和1,3-(二-O-n-烷基)甘油衍生物及其药学上可接受的酸盐作为细胞介导免疫的非特异性刺激剂是有用的。
• Antiviral amine derivatives of glycerol and propanediols
  申请人：Pfizer Inc.

  公开号：US04166132A1

  公开（公告）日：1979-08-28

  Novel amine and amidine derivatives of di-0-(n-higher alkyl and alkenyl)-glycerols and -propanediols, and their pharmaceutically acceptable acid addition salts, are useful for combating viral infections in mammals. Of particular interest is 1,3-di-0-(n-hexadecyl)-2-0-(3-aminopropyl)-glycerol, and its pharmaceutically acceptable acid addition salts.

  新型的二0-(n-高级脂肪烷基和烯基)-甘油和-丙二醇的胺和酰胺衍生物，及其药学上可接受的酸盐，可用于治疗哺乳动物的病毒感染。特别感兴趣的是1,3-二0-(n-十六烷基)-2-0-(3-氨基丙基)-甘油及其药学上可接受的酸盐。
• Imidazole-Based pH-Sensitive Convertible Liposomes for Anticancer Drug Delivery
  作者：Ruiqi Huang、Vijay Gyanani、Shen Zhao、Yifan Lu、Xin Guo

  DOI：10.3390/ph15030306

  日期：——

  In efforts to enhance the activity of liposomal drugs against solid tumors, three novel lipids that carry imidazole-based headgroups of incremental basicity were prepared and incorporated into the membrane of PEGylated liposomes containing doxorubicin (DOX) to render pH-sensitive convertible liposomes (ICL). The imidazole lipids were designed to protonate and cluster with negatively charged phosphatidylethanolamine-polyethylene glycol when pH drops from 7.4 to 6.0, thereby triggering ICL in acidic tumor interstitium. Upon the drop of pH, ICL gained more positive surface charges, displayed lipid phase separation in TEM and DSC, and aggregated with cell membrane-mimetic model liposomes. The drop of pH also enhanced DOX release from ICL consisting of one of the imidazole lipids, sn-2-((2,3-dihexadecyloxypropyl)thio)-5-methyl-1H-imidazole. ICL demonstrated superior activities against monolayer cells and several 3D MCS than the analogous PEGylated, pH-insensitive liposomes containing DOX, which serves as a control and clinical benchmark. The presence of cholesterol in ICL enhanced their colloidal stability but diminished their pH-sensitivity. ICL with the most basic imidazole lipid showed the highest activity in monolayer Hela cells; ICL with the imidazole lipid of medium basicity showed the highest anticancer activity in 3D MCS. ICL that balances the needs of tissue penetration, cell-binding, and drug release would yield optimal activity against solid tumors.

  为了增强脂质体药物对实体肿瘤的活性，制备了三种新型脂质体，它们携带具有递增碱性的咪唑基头基，并被纳入PEG化脂质体膜中，其中含有多柔比星(DOX)，以形成pH敏感的可转换脂质体(ICL)。咪唑脂质体被设计为在pH从7.4降至6.0时质子化并与带负电荷的磷脂酰乙醇胺-聚乙二醇簇集，从而在酸性肿瘤间质中触发ICL。pH下降后，ICL表面带正电荷增多，在TEM和DSC中显示脂质相分离，并与细胞膜模拟模型脂质体聚集。pH下降还增强了由咪唑脂质体之一，sn-2-((2,3-二十六烷氧基丙基)硫基)-5-甲基-1H-咪唑构成的ICL中多柔比星的释放。ICL对单层细胞和几种3D MCS表现出比类似PEG化、pH不敏感的含多柔比星脂质体（作为对照和临床基准）更优越的活性。胆固醇的存在增强了ICL的胶体稳定性，但降低了它们的pH敏感性。咪唑脂质体中最基础的ICL在单层Hela细胞中表现出最高的活性；碱性中等的咪唑脂质体ICL在3D MCS中表现出最高的抗癌活性。平衡组织穿透、细胞结合和药物释放需求的ICL将产生最佳的实体肿瘤活性。
• Peptidderivate, Verfahren zu deren Herstellung und Zwischenprodukte sowie pharmazeutische Präparate mit einer dieser Verbindungen
  申请人：CIBA-GEIGY AG

  公开号：EP0014815A2

  公开（公告）日：1980-09-03

  Die Erfindung betrifft Lipopeptide der Formel worin R1 einen aliphatischen oder aliphatisch-cycloaliphatischen Kohlenwasserstoffrest mit mindestens 9 C-Atomen oder einen aliphatischen Acylrest mit 12-21 C-Atomen oder den 5-Cholesten-3-yl-Rest bedeutet, wobei im genannten Kohlenwasserstoff- oder Acylrest die C-Atom-Kette auch durch Sauerstoffgruppen unterbrochen sein kann, und/oder worin als Substituenten maximal eine freie oder mit einer monobasischen Carbonsäure veresterte Hydroxylgruppe vorhanden sein können, und X eine peptidisch gebundene freie, veresterte oder amidierte Aminosäure oder eine Aminosäurensequenz von 2-10 Aminosäuren, deren terminale Carboxylgruppe in freier, veresterter oder amidierter Form vorliegt, bedeutet, und Diastereomerengemische dieser Verbindungen, Salze und Komplexe. Die neuen Verbindungen besitzen eine ausgesprochene immunpotenzierende Wirkung. Sie können synthetisch, z.B. durch Einführung der Gruppe X der obigen Formel in entsprechende Carbonsäuren nach üblichen Methoden der Peptidchemie hergestellt werden.

  本发明涉及式如下的脂肽 其中 R1 表示至少具有 9 个碳原子的脂肪族或脂肪族-环脂族烃基，或具有 12-21 个碳原子的脂肪族酰基，或 5-胆甾烯-3-基，所述烃基或酰基中的碳原子链也可能被氧基团打断、和/或其中最多可有一个游离羟基或羟基与一元羧酸酯化作为取代基，X 表示与肽结合的游离、酯化或酰胺化氨基酸或其末端羧基以游离、酯化或酰胺化形式存在的 2-10 个氨基酸的氨基酸序列，以及这些化合物的非对映混合物、盐和络合物。 新化合物具有明显的免疫增强作用。它们可以通过合成方法制得，例如，使用肽化学的常规方法将上式中的基团 X 引入相应的羧酸中。
• DE2835369
  申请人：——

  公开号：——

  公开（公告）日：——