Octadecanoic acid 2-hexadecylsulfanyl-1-hydroxymethyl-ethyl ester | 91404-23-8

• 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: Octadecanoic acid 2-hexadecylsulfanyl-1-hydroxymethyl-ethyl ester
• CAS: 91404-23-8
• 化学式: C₃₇H₇₄O₃S
• 分子量: 599.059
• InChiKey: QJLGEGUEOKYIDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.37
• 重原子数：
  41.0
• 可旋转键数：
  35.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Octadecanoic acid 2-hexadecylsulfanyl-1-hydroxymethyl-ethyl ester 在 水 、 三乙胺 、 三氯氧磷 作用下， 生成 rac-1-S-hexadecyl-2-O-stearoyl-1-thioglycerol 3-phosphate
  参考文献：
  名称：

  Nucleoside conjugates. 13. Synthesis and antitumor activity of 1-.beta.-D-arabinofuranosylcytosine conjugates of thioether lipids with improved water solubility

  摘要：

  A series of ara-CDP-rac-1-S-alkyl-2-0-acyl-1-thioglycerols (3-12), analogues of highly active Cytoros2 (1), was prepared, and solubility, lipophilicity, and structure-activity relationships of these conjugates were investigated. The conjugates with sn-1 alkyl (C14) and the sn-2 fatty acyl (>C16) were sparingly soluble. The latter formed micelles upon sonication. Conjugate 7 containing the sn-1 tetradecyl and the sn-2 palmitoyl (C16) groups formed micelles by both sonication and shaking. The partition coefficients (1-octanol/PBS) of the water-soluble conjugates were about 20 times greater than that of ara-C. The water-insoluble showed a more than 40 times increase. A single dose of the micelle-forming conjugates 7 and 10 produced a significant increase in life span (ILS >421 %) with 50 % long-term survivors (>45 days) in mice bearing ip-implanted L1210 lymphoid leukemia. These results were comparable to those of previous micelle-forming conjugate 1 (Cytoros). In contrast, the water-soluble conjugates at single doses were less effective (ILS 81-386% with 0-33% long-term survivors). However, three divided doses of the water-soluble conjugates were found to be as effective as a single dose of micellar solution of the water-insoluble. The results indicate that conjugate 7 and most of the water-soluble derivatives warrant further investigation.

  DOI：

  10.1021/jm00064a012
• 作为产物：
  描述：

  溴代十六烷 在 吡啶 、 咪唑 、 氢氧化钾 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 102.0h， 生成 Octadecanoic acid 2-hexadecylsulfanyl-1-hydroxymethyl-ethyl ester
  参考文献：
  名称：

  Nucleoside conjugates. 13. Synthesis and antitumor activity of 1-.beta.-D-arabinofuranosylcytosine conjugates of thioether lipids with improved water solubility

  摘要：

  A series of ara-CDP-rac-1-S-alkyl-2-0-acyl-1-thioglycerols (3-12), analogues of highly active Cytoros2 (1), was prepared, and solubility, lipophilicity, and structure-activity relationships of these conjugates were investigated. The conjugates with sn-1 alkyl (C14) and the sn-2 fatty acyl (>C16) were sparingly soluble. The latter formed micelles upon sonication. Conjugate 7 containing the sn-1 tetradecyl and the sn-2 palmitoyl (C16) groups formed micelles by both sonication and shaking. The partition coefficients (1-octanol/PBS) of the water-soluble conjugates were about 20 times greater than that of ara-C. The water-insoluble showed a more than 40 times increase. A single dose of the micelle-forming conjugates 7 and 10 produced a significant increase in life span (ILS >421 %) with 50 % long-term survivors (>45 days) in mice bearing ip-implanted L1210 lymphoid leukemia. These results were comparable to those of previous micelle-forming conjugate 1 (Cytoros). In contrast, the water-soluble conjugates at single doses were less effective (ILS 81-386% with 0-33% long-term survivors). However, three divided doses of the water-soluble conjugates were found to be as effective as a single dose of micellar solution of the water-insoluble. The results indicate that conjugate 7 and most of the water-soluble derivatives warrant further investigation.

  DOI：

  10.1021/jm00064a012