2-O-Benzyl-1-O-octadecyl-sn-glycero-3-phosphorylcholin | 80483-86-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: 2-O-Benzyl-1-O-octadecyl-sn-glycero-3-phosphorylcholin
• 英文别名: (2R)-2-Benzyloxy-3-octadecyloxypropyl 2-trimethylammonioethyl phosphate；[(2R)-3-octadecoxy-2-phenylmethoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 80483-86-9
• 化学式: C₃₃H₆₂NO₆P
• 分子量: 599.832
• InChiKey: LLVFHZWPRVDZBY-MGBGTMOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  41
• 可旋转键数：
  29
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-O-Benzyl-1-O-octadecyl-sn-glycero-3-phosphorylcholin 在 1,3-丙二醇 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以100%的产率得到Γ-O-十八烷基-L-Α-溶血卵磷脂
  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
• 作为产物：
  描述：

  硬脂醇 在 lithium aluminium tetrahydride 、 三氟甲磺酸 、 三氟化硼乙醚 、 三乙胺 、 三氯氧磷 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 4.67h， 生成 2-O-Benzyl-1-O-octadecyl-sn-glycero-3-phosphorylcholin
  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

• 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。
• An enantioselective synthesis of platelet-activating factors, their enantiomers, and their analogues from D- and L-tartaric acids.
  作者：MASAJI OHNO、KAGARI FUJITA、HISAO NAKAI、SUSUMU KOBAYASHI、KEIZO INOUE、SHOSHICHI NOJIMA

  DOI：10.1248/cpb.33.572

  日期：——

  Acetyl glyceryl ether phosphorylcholines (platelet-activating factors ; PAFs), their enantiomers, and their analogues were efficiently synthesized in a stereochemically unambiguous manner starting from D-and L-tartaric acids as chiral synthons. The enantiomer of C16-PAF (S-comfiguration) showed far less activity than the natural PAF (R-configuration), and the N-methylpiperidine and N-methylpyrrolidine analogues were found to possess much higher activity than natural C16-PAF.

  乙酰甘油醚磷脂酰胆碱（血小板激活因子；PAFs）、其对映体及其类似物以立体化学明确的方式有效合成，起始于D-和L-酒石酸作为手性合成前体。C16-PAF的对映体（S-构型）显示出远低于天然PAF（R-构型）的活性，而N-甲基哌啶和N-甲基吡咯烷的类似物则显示出比天然C16-PAF更高的活性。
• Glycerol derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0094186A1

  公开（公告）日：1983-11-16

  Glycerol derivatives, inclusive of salts thereof, of the formula wherein R1 is alkyl or alkylcarbamoyl containing 10 to 30 carbon atoms, R2 and R3 are independently hydrogen, C1-6 alkyl or, taken toaether with the adiacent nitrogen atom form cyclic amino, and epresents cyclic ammonio, and of the formula wherein R1 is as defined above, R2' and R3' are C1-6 alkyl or, taken together with the adjacent nitrogen atom, form cyclic amino and R4' R5' and R6' are independently hydrogen or C1-6 alkyl, are useful as antihypertensive agents.

  甘油衍生物，包括其盐，其式为 其中 R1 是含有 10 至 30 个碳原子的烷基或烷基氨基甲酰基，R2 和 R3 独立地是氢、C1-6 烷基或与邻接的氮原子形成环氨基的醚，以及 代表环氨，其式如下 其中 R1 如上定义，R2'和 R3'为 C1-6 烷基或与邻近的氮原子形成环氨基，R4'、R5'和 R6'独立地为氢或 C1-6 烷基。
• TSUSHIMA, SUSUMU;NISHIKAWA, KOHEI
  作者：TSUSHIMA, SUSUMU、NISHIKAWA, KOHEI

  DOI：——

  日期：——
• TSUSIMA, SUSUMU;NISIKAVA, KOXEHJ
  作者：TSUSIMA, SUSUMU、NISIKAVA, KOXEHJ

  DOI：——

  日期：——