1-octadecylthio-rac-glycerol | 7400-44-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-octadecylthio-rac-glycerol
• 英文别名: 1-S-octadecyl-rac-thioglycerol；DL-thiobatyl alcohol；octadecylthio-1 propanediol-2,3；(+/-)-2.3-Dihydroxypropyl-octadecyl-sulfid；Thiobatylalkohol, 2.3-Dihydroxypropyl-octadecan-sulfid；3-octadecylsulfanyl-propane-1,2-diol；3-Octadecylsulfanylpropane-1,2-diol
• CAS: 7400-44-4
• 化学式: C₂₁H₄₄O₂S
• 分子量: 360.645
• InChiKey: WHCHVADSXPASOY-UHFFFAOYSA-N

物化性质

• 沸点：
  489.8±25.0 °C(Predicted)
• 密度：
  0.937±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  24
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  65.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-octadecylthio-rac-glycerol 在 吡啶 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 (1-octadecylsulfanyl-3-trityloxypropan-2-yl) hexadecanoate
  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：

  十八硫醇 在 盐酸 、 sodium hydroxide 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 11.0h， 生成 1-octadecylthio-rac-glycerol
  参考文献：
  名称：

  Malina, E.V.; Serebrennikova, G.A.; Evstigneeva, R.P., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 840 - 841

  摘要：

  DOI：

文献信息

• Synthesis of sulfur analogs of alkyl lysophospholipid and neoplastic cell growth inhibitory properties
  作者：Susan Morris-Natschke、Jefferson R. Surles、Larry W. Daniel、Michael E. Berens、Edward J. Modest、Claude Piantadosi

  DOI：10.1021/jm00160a055

  日期：1986.10

  Five sulfur-containing phospholipid analogues (compounds 1-5) of alkyl lysophospholipid (1-O-alkyl-2-O-methyl-rac-glycero-3-phosphocholine, ALP) were synthesized and tested for inhibition of neoplastic cell proliferation with two human ovarian carcinoma cell lines in a clonogenic assay and with the HL-60 promyelocytic leukemia cell line. Compared with 1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine

  合成了五个烷基溶血磷脂（1-O-烷基-2-O-甲基-rac-甘油-3-磷酸胆碱，ALP）的含硫磷脂类似物（化合物1-5），并用两种方法测试了对肿瘤细胞增殖的抑制作用人卵巢癌细胞系的克隆形成分析以及HL-60早幼粒细胞白血病细胞系。与最活跃的参考类似物1-O-十八烷基-2-O-甲基-rac-甘油-3-磷酸胆碱（ET-18-OMe）相比，这些硫代类似物对HL-60细胞的活性至少相同。 1-S-十六烷基-2-O-乙基类似物（2）在克隆形成测定中的活性是其两倍。
• Polyhydroxyl monosulfoxide surfactant
  申请人：L'Oreal

  公开号：US03984480A1

  公开（公告）日：1976-10-05

  A polyhydroxyl monosulfoxide surfactant, usefully employed, for instance, in a cosmetic composition such as a shampoo, a hair dye formulation or a bath foam composition, has the formula ##EQU1## wherein R is selected from the group consisting of linear or branched aliphatic saturated or unsaturated hydrocarbon having 8-22 carbon atoms, alkylbenzyl having 8-22 carbon atoms and mixtures thereof, and n has a statistical mean value greater than 1 and equal to or less than 10, and preferably 2-7.

  一种聚羟基单亚磺酰氧表面活性剂，可用于化妆品组合物中，例如洗发水、染发配方或泡沫浴组合物中，其化学式为##EQU1##其中R选自直链或支链饱和或不饱和烃基，其碳原子数为8-22，烷基苯基的碳原子数为8-22，以及它们的混合物，n的统计平均值大于1且等于或小于10，最好为2-7。
• Stabilized compositions containing hindered hydroxyalkanoates
  申请人：Ciba-Geigy Corporation

  公开号：US04058502A1

  公开（公告）日：1977-11-15

  The compounds are esters having the formula ##STR1## wherein R.sub.1 is alkyl, cycloalkyl, alkylthioethyl or alkylpolyoxyalkylene, Z is oxygen or sulfur, R.sub.2 is the group ##STR2## R.sub.3 is hydrogen, alkyl, cycloalkyl, or .alpha.-methylbenzyl, R.sub.4 is alkyl or cycloalkyl, R.sub.5 is hydrogen or alkyl, provided when R.sub.3 is hydrogen, R.sub.5 is alkyl and R.sub.4 is located on the carbon atom ortho to the hydroxyl group, and A is a covalent carbon bond or lower alkylene.

  这些化合物是酯类，其化学式为##STR1## 其中R.sub.1是烷基、环烷基、烷基硫乙基或烷基聚氧烷基，Z是氧或硫，R.sub.2是##STR2## R.sub.3是氢、烷基、环烷基或α-甲基苄基，R.sub.4是烷基或环烷基，R.sub.5是氢或烷基，当R.sub.3是氢时，R.sub.5是烷基，且R.sub.4位于对羟基的碳原子上，A是共价碳键或较低的烷基。
• Polyhydroxyl monosulfoxide shampoo compositions
  申请人：L'Oreal

  公开号：US04058629A1

  公开（公告）日：1977-11-15

  A polyhydroxyl monosulfoxide surfactant, usefully employed, for instance, in a cosmetic composition such as a shampoo, a hair dye formulation or a bath foam composition, has the formula ##STR1## wherein R is selected from the group consisting of linear or branched aliphatic saturated or unsaturated hydrocarbon having 8-22 carbon atoms, alkylbenzyl having 8-22 carbon atoms and mixtures thereof, and n has a statistical mean value greater than 1 and equal to or less than 10, and preferably 2-7.

  一种多羟基单亚砜表面活性剂，可用于化妆品组合物，例如洗发水、染发制剂或泡沫浴组合物中，其化学式为 ##STR1## 其中R选自具有8-22个碳原子的线性或支链脂肪饱和或不饱和烃，具有8-22个碳原子的烷基苯和它们的混合物，n的统计平均值大于1且等于或小于10，最好为2-7。
• Garrigues, Bernard; Bertrand, Guy; Frehel, Daniel, Phosphorus and Sulfur and the Related Elements, 1984, vol. 21, p. 171 - 176
  作者：Garrigues, Bernard、Bertrand, Guy、Frehel, Daniel、Maffrand, Jean-Pierre

  DOI：——

  日期：——