rac-1-S-octadecyl-2-O-palmitoyl-1-thioglycerol | 125592-19-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: rac-1-S-octadecyl-2-O-palmitoyl-1-thioglycerol
• 英文别名: (1-Hydroxy-3-octadecylsulfanylpropan-2-yl) hexadecanoate
• CAS: 125592-19-0
• 化学式: C₃₇H₇₄O₃S
• 分子量: 599.059
• InChiKey: YCJRVNPMTWEGMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.3
• 重原子数：
  41
• 可旋转键数：
  36
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  rac-1-S-octadecyl-2-O-palmitoyl-1-thioglycerol 在 三乙胺 、 三氯氧磷 作用下， 以 正己烷 、 甲苯 为溶剂， 以44.7%的产率得到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
• 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 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 126.0h， 生成 rac-1-S-octadecyl-2-O-palmitoyl-1-thioglycerol
  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

• 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：——
• Nucleoside conjugates. 11. Synthesis and antitumor activity of 1-.beta.-D-arabinofuranosylcytosine and cytidine conjugates of thioether lipids
  作者：Chung Il Hong、Alan J. Kirisits、Alexander Nechaev、David J. Buchheit、Charles R. West

  DOI：10.1021/jm00167a016

  日期：1990.5

  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.