rac-1-S-octadecyl-2-palmitoyl-1-thioglycerol 3-phosphate | 125592-21-4

• 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: rac-1-S-octadecyl-2-palmitoyl-1-thioglycerol 3-phosphate
• 英文别名: rac-1-S-octadecyl-2-O-palmitoyl-1-thioglycerol 3-phosphate；(1-octadecylsulfanyl-3-phosphonooxypropan-2-yl) hexadecanoate
• CAS: 125592-21-4
• 化学式: C₃₇H₇₅O₆PS
• 分子量: 679.039
• InChiKey: MQLORAQPSGEMEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.2
• 重原子数：
  45
• 可旋转键数：
  38
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  rac-1-S-octadecyl-2-palmitoyl-1-thioglycerol 3-phosphate 、 Morpholin-4-yl-phosphonic acid mono-[(2S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester 在 吡啶 作用下， 反应 168.0h， 生成 2',3'-dideoxycytidine 5'-diphosphorate-rac-1-S-octadecyl-O-palmitoyl-1-thioglycerol
  参考文献：
  名称：

  核苷结合物。15.醚和硫醚磷脂的抗HIV核苷缀合物的合成和生物学活性。

  摘要：

  已合成了一系列通过焦磷酸二酯键连接的（1-O-烷基）和硫醚（1-S-烷基）脂质的抗HIV核苷共轭物，作为核苷的胶束形成前药，以提高其治疗效率。这些包括AZT 5'-二磷酸-rac-1-S-十八烷基-2-O-棕榈酰-1-硫甘油（1），3'-叠氮基2'，3'-二脱氧尿苷5'-二磷酸-rac-1- S-十八烷基-2-O-棕榈酰基-1-硫甘油（2）2'，3'-二脱氧胞苷5'-二磷酸-rac-1-S-十八烷基-2-O-棕榈酰基-1-硫甘油（3）和AZT 5'-二磷酸酯-rac-1-O-十四烷基-2-O-棕榈酰甘油（4）。缀合物通过超声处理形成胶束（平均直径范围为6.8-55.5 nm）。结合物1可以保护80％的HIV感染CEM细胞（低至0.58 microM），并由于普遍的细胞毒性而在180 microM时失去保护，而结合物在100 microM时开始显示出细胞毒性。药代动力学研究表明，偶联物1和2

  DOI：

  10.1021/jm950620o
• 作为产物：
  描述：

  硬脂基溴 在 吡啶 、 咪唑 、 氢氧化钾 、 四丁基氟化铵 、 溶剂黄146 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 126.0h， 生成 rac-1-S-octadecyl-2-palmitoyl-1-thioglycerol 3-phosphate
  参考文献：
  名称：

  Nucleoside conjugates. 11. Synthesis and antitumor activity of 1-.beta.-D-arabinofuranosylcytosine and cytidine conjugates of thioether lipids

  摘要：

  Five 1-beta-D-arabinofuranosylcytosine conjugates and two cytidine conjugates of thioether lipids (1-S-alkylthioglycerols) linked by a pyrophosphate diester bond have been prepared and their antitumor activity against an ara-C2 sensitive (L1210/0) and two ara-C resistant L1210 lymphoid leukemia sublines in mice were evaluated. These prodrugs of ara-C include ara-CDP-rac-1-S-hexadecyl-2-O-palmitoyl-1-thioglycerol (8a), ara-CDP-rac-1-S-octadecyl-2-O-palmitoylthioglycerol (8b), and ara-CDP-rac-1-S-octadecyl-2-O-methyl(or -ethyl, -hexadecyl)thioglycerols (8c-e). The cytidine conjugates include CDP-rac-1-S-octadecyl-2-O-palmitoyl(or -methyl)- 1-thioglycerols (9a and 9b). Sonicated solutions of the conjugates existed in the form of micellar disks (size 0.01-0.04 microns). Single doses (200-400 mg/kg) of 8a and 8b produced significant increase in life span (257-371%) in mice bearing ip implanted L1210/0 leukemia. In contrast, conjugates 8c-e were less effective (ILS 19-75%) and cytidine conjugates (9a and 9b) were ineffective. Even though 8a and 8b were found to be curative in a high percentage of mice bearing ip implanted partially ara-C resistant L1210 subline [L1210/ara-C(I)], they were completely ineffective against deoxycytidine kinase deficient ara-C resistant L1210 subline [L1210/ara-C(II)]. However, the present results, together with the previous, demonstrate that 8a and 8b are promising new prodrugs of ara-C with improved efficacy.

  DOI：

  10.1021/jm00167a016

文献信息

• Nucleoside 5'-diphosphate conjugates of ether lipids
  申请人：Health Research, Inc.

  公开号：US05484911A1

  公开（公告）日：1996-01-16

  A compound which exhibits antiviral activity having the formula: ##STR1## wherein; R.sub.1 is selected from the group consisting of alkyls and alkenyls containing from 8 to 22 carbon atoms; A is selected from the group consisting of O and S atoms; R.sub.2 is selected from the group consisting of alkyls and alkenyls containing from 8 to 22 carbon atoms; and the Nucleoside is selected from the group consisting of 2',3'-dideoxynucleosides, 3'-azido-2',3'-dideoxynucleosides, and 2',3'-didehydro-2',3'-dideoxynucleosides.

  具有抗病毒活性的化合物的化学式为：##STR1## 其中; R.sub.1选自含有8至22个碳原子的烷基和烯基组成的群体; A选自O和S原子组成的群体; R.sub.2选自含有8至22个碳原子的烷基和烯基组成的群体; 核苷酸选自2'，3'-二脱氧核苷酸，3'-氮杂基-2'，3'-二脱氧核苷酸和2'，3'-二脱氢-2'，3'-二脱氧核苷酸。
• HONG, CHUNG IL;KIRISITS, ALAN J.;NECHAEV, ALEXANDER;BUCHHEIT, DAVID J.;WE+, J. MED. CHEM., 33,(1990) N, C. 1380-1386
  作者：HONG, CHUNG IL、KIRISITS, ALAN J.、NECHAEV, ALEXANDER、BUCHHEIT, DAVID J.、WE+

  DOI：——

  日期：——