3-(hexadecyloxy)-2-ethoxy-1-propanol | 92758-87-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 3-(hexadecyloxy)-2-ethoxy-1-propanol
• 英文别名: 1-O-hexadecyl-2-O-ethylglycerol；rac-1-Hexadecyloxo-2-ethoxy-3-hydroxypropane；2-ethoxy-3-hexadecoxypropan-1-ol
• CAS: 92758-87-7
• 化学式: C₂₁H₄₄O₃
• 分子量: 344.579
• InChiKey: XNJPJQWHGJPRGN-UHFFFAOYSA-N

物化性质

• 沸点：
  444.2±25.0 °C(Predicted)
• 密度：
  0.893±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 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：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(hexadecyloxy)-2-ethoxy-1-propanol 在 四溴化碳 、 三苯基膦 作用下， 生成 1-(hexadecyloxy)-2-ethoxy-3-bromopropane
  参考文献：
  名称：

  具有细胞毒活性的新型亲脂四胺的合成

  摘要：

  合成了新的亲脂性多胺，其中天然或合成的四胺通过末端NH2基团连接至甘油二酸酯和/或短链脂族取代基，并测试了它们的细胞毒活性。评价了合成化合物的结构与其细胞毒性和溶血作用之间的关系。

  DOI：

  10.1016/j.mencom.2019.11.003
• 作为产物：
  描述：

  2-ethoxy-1,3-propanediol 、 溴代十六烷 以 甲苯 为溶剂， 以45%的产率得到3-(hexadecyloxy)-2-ethoxy-1-propanol
  参考文献：
  名称：

  Kertscher; Ostermann, Pharmazie, 1987, vol. 42, # 11, p. 713 - 715

  摘要：

  DOI：

文献信息

• Synthesis of phosphocholine and quaternary amine ether lipids and evaluation of in vitro antineoplastic activity
  作者：Susan L. Morris-Natschke、Fatma Gumus、Canio J. Marasco、Karen L. Meyer、Michael Marx、Claude Piantadosi、Matthew D. Layne、Edward J. Modest

  DOI：10.1021/jm00066a011

  日期：1993.7

  methyl decreased activity slightly. In the nonphosphorus compounds, many nitrogen heterocycles and also a sulfonium moiety were incorporated without changing the degree of activity; however, a thiazolium group decreased activity. The most active compound, 29 [N-[3-(hexadecyloxy)-2-methoxypropyl]-3-(hydroxymethyl)pyridinium bromide], was approximately twice as active as the reference standard, ET-18-OMe

  在HL-60早幼粒细胞系中已评估了许多含磷（例如，磷胆碱）和非含磷（例如，季铵盐）醚脂质的体外抗肿瘤活性。这些化合物是ET-18-OMe（1-O-十八烷基-2-O-甲基-rac-甘油-3-磷酸胆碱）的类似物。1-（烷基酰胺基）-，-（烷硫基）-和-（烷氧基）丙基主链的结构修饰提供了对这些脂质的结构-活性关系的进一步了解。在这项研究中，优选长饱和的C-1链和带有单个短C-2取代基的三碳主链。在磷胆碱带正电的氮原子上，少于三个取代基会导致活性显着下降，大于甲基的取代基会略微降低活性。在无磷化合物中，在不改变活性程度的情况下，引入了许多氮杂环以及also部分。但是，噻唑鎓组降低了活性。在台盼蓝中，活性最高的化合物29 [N- [3-（十六烷基氧基）-2-甲氧基丙基] -3-（羟甲基）吡啶鎓溴]的活性约为参考标准ET-18-OMe的两倍。染料排除试验。
• In vitro evaluation of phosphocholine and quaternary ammonium containing lipids as novel anti-HIV agents
  作者：Karen L. Meyer、Canino J. Marasco、Susan L. Morris-Natschke、Khalid S. Ishaq、Claude Piantadosi、Louis S. Kucera

  DOI：10.1021/jm00108a021

  日期：1991.4

  A series of synthetic lipids containing a two- or three-carbon backbone substituted with a thio, oxy, or amidoalkyl functionality and either a phosphocholine or quaternary ammonium moiety was evaluated as potential anti-HIV-1 agents. Several analogues were identified as possessing activity with the most promising compound being rac-3-octadecanamido-2-ethoxypropylphosphocholine (8). Compound 8 exhibited an IC50 for the inhibition of plaque formation of 0.16-mu-M which was 84-fold lower than the IC50 value determined for CEM-SS cell growth inhibition. Initial mechanistic studies have indicated that these compounds, unlike AZT, are not reverse transcriptase (RT) inhibitors, but instead appear to inhibit a late step in HIV replication involving virus assembly and infectious virus production. Since these lipids are acting via a different mechanism, they represent an alternative approach to the chemotherapeutic treatment of AIDS as well as candidates for combination therapy with AZT.
• Synthesis and evaluation of novel ether lipid nucleoside conjugates for anti-HIV-1 activity
  作者：Claude Piantadosi、Canio J. Marasco、Susan L. Morris-Natschke、Karen L. Meyer、Fatma Gumus、Jefferson R. Surles、Khalid S. Ishaq、Louis S. Kucera、Nathan Iyer

  DOI：10.1021/jm00108a025

  日期：1991.4

  Combinations of an amidoalkylphosphocholine, 8, and AZT have been found to cause an apparent synergistic action in suppressing infectious HIV-1 replication. In addition, amidoalkyl, oxyalkyl, and thioalkyl ether lipids have been chemically linked to anti-HIV-1 nucleosides (AZT and DDI) through phosphate and phosphonate linkages. These conjugates have shown promising in vitro anti-HIV-1 activity. Also, the conjugates have a 5-10-fold reduction in cell cytotoxicity compared to AZT alone. The most active compound, an amidoalkyl ether lipid-AZT conjugate, 4A, was found to have a differential selectivity of 1793 in a syncytial plaque assay. In comparison, AZT alone has a value of 1281.
• Synthesis of quaternary amine ether lipids and evaluation of neoplastic cell growth inhibitory properties
  作者：Susan L. Morris-Natschke、Karen L. Meyer、Canio J. Marasco、Claude Piantadosi、Fiona Rossi、Patrick L. Godwin、Edward J. Modest

  DOI：10.1021/jm00168a042

  日期：1990.6

  Novel quaternary amine ether lipids have been synthesized and tested for inhibition of neoplastic cell proliferation with the HL-60 promyelocytic leukemia cell line. These compounds contain a positively charged quaternary amine functional group attached either directly to the glycerol backbone or at the end of an alkoxy chain. The biological testing has identified several analogues with activity equivalent to or greater than that exhibited by the reference compound in this assay, ET-18-OMe (1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine). Among the most active analogues are compounds 11, [N,N,N-triethyl-3-(hexadecyloxy)-2-ethoxy-1-propylammonium bromide] and 22 [N-[4-[3-(hexadecyloxy)-2-ethoxypropoxy]-1-butyl]pyridinium bromide], which are approximately 3 times as active as the reference standard.
• Kertscher; Ostermann, Pharmazie, 1991, vol. 46, # 10, p. 708 - 711
  作者：Kertscher、Ostermann

  DOI：——

  日期：——