(+/-)-1-S-hexadecyl-2-O-ethyl-3-O-mesylthioglycerol | 124581-73-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (+/-)-1-S-hexadecyl-2-O-ethyl-3-O-mesylthioglycerol
• 英文别名: (2-ethoxy-3-hexadecylsulfanylpropyl) methanesulfonate
• CAS: 124581-73-3
• 化学式: C₂₂H₄₆O₄S₂
• 分子量: 438.737
• InChiKey: HPTGHFFBODPNAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  28
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-1-S-hexadecyl-2-O-ethyl-3-O-mesylthioglycerol 在 lithium bromide 作用下， 以 丙酮 为溶剂， 反应 36.0h， 生成 1-(hexadecyloxy)-2-ethoxy-3-bromopropane
  参考文献：
  名称：

  Synthesis of quaternary amine ether lipids and evaluation of neoplastic cell growth inhibitory properties

  摘要：

  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.

  DOI：

  10.1021/jm00168a042
• 作为产物：
  描述：

  1-S-hexadecyl-3-O-trityl-rac-thioglycerol 在 sodium hydride 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 73.0h， 生成 (+/-)-1-S-hexadecyl-2-O-ethyl-3-O-mesylthioglycerol
  参考文献：
  名称：

  新型的烷基甘油季铵盐衍生物作为蛋白激酶C的有效抑制剂的合成及生物活性

  摘要：

  烷基甘油，例如rac-1-O-十八烷基-2-O-甲基甘油磷酸胆碱（Et-18-OMe）对多种癌细胞系的转移和生长均显示出抑制作用。已显示烷基磷脂积聚在几种细胞系的表面，其选择性仍不清楚。该作用的结果可能导致抑制细胞膜相关蛋白激酶C（PKC）。这项研究的目的是开发PKC的醚脂质抑制剂以增强抗肿瘤活性。这导致了一系列烷基甘油的新型季铵衍生物的合成和体外测试。这些类似物在用rac-1-O-油酰基-2-O-乙酰甘油刺激的PKC上的生物学测试表明，其抑制作用与Et-18-OMe相当。

  DOI：

  10.1021/jm00165a016

文献信息

• Quaternary amine containing ether or ester lipid derivatives and
  申请人：Wake Forest University

  公开号：US05614548A1

  公开（公告）日：1997-03-25

  Quaternary amine-containing ether lipid analogs of the formula R.sub.1 --X--R.sub.2 --N.sup.+ (R.sub.3) (R.sub.4) (R.sub.5) Z.sup.- are disclosed. R.sub.1 represents a hydrophobic group and R.sub.2 represents the backbone of the molecule, with the quaternary amine being linked directly to the backbone. Pharmaceutical compositions including these compounds and methods of combating tumors with these compounds are disclosed. Also disclosed is a method of combating viral infections with both these compounds and ET-18-OMe and its analogs.

  公开了式子为R.sub.1 -X-R.sub.2 -N.sup.+ (R.sub.3) (R.sub.4) (R.sub.5) Z.sup.-的四元胺含有醚脂类似物。R.sub.1代表疏水基团，R.sub.2代表分子的骨架，四元胺直接连接到骨架上。公开了包括这些化合物的制药组合物和使用这些化合物对抗肿瘤的方法。还公开了使用这些化合物和ET-18-OMe及其类似物对抗病毒感染的方法。
• MARASCO, CANIO J. (JR);PIANTADOSI, CLAUDE;MEYER, KAREN L.;MORRIS-NATSCHKE+, J. MED. CHEM., 33,(1990) N, C. 985-992
  作者：MARASCO, CANIO J. (JR)、PIANTADOSI, CLAUDE、MEYER, KAREN L.、MORRIS-NATSCHKE+

  DOI：——

  日期：——
• Synthesis and biological activity of novel quaternary ammonium derivatives of alkylglycerols as potent inhibitors of protein kinase C
  作者：Canio J. Marasco、Claude Piantadosi、Karen L. Meyer、Susan Morris-Natschke、Khalid S. Ishaq、George W. Small、Larry W. Daniel

  DOI：10.1021/jm00165a016

  日期：1990.3

  effect on the metastasis and growth of various cancer cell lines. Alkyl phospholipids have been shown to accumulate at the surface in several cell lines, the selectivity of which is still not clearly understood. A consequence of this action may lead to the inhibition of cell membrane related protein kinase C (PKC). The goal of this research was to develop ether lipid inhibitors of PKC to augment antineoplastic

  烷基甘油，例如rac-1-O-十八烷基-2-O-甲基甘油磷酸胆碱（Et-18-OMe）对多种癌细胞系的转移和生长均显示出抑制作用。已显示烷基磷脂积聚在几种细胞系的表面，其选择性仍不清楚。该作用的结果可能导致抑制细胞膜相关蛋白激酶C（PKC）。这项研究的目的是开发PKC的醚脂质抑制剂以增强抗肿瘤活性。这导致了一系列烷基甘油的新型季铵衍生物的合成和体外测试。这些类似物在用rac-1-O-油酰基-2-O-乙酰甘油刺激的PKC上的生物学测试表明，其抑制作用与Et-18-OMe相当。
• 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.