Toluene-4-sulfonic acid 2-hexadecyloxy-ethyl ester | 171364-92-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Toluene-4-sulfonic acid 2-hexadecyloxy-ethyl ester
• 英文别名: Ethanol, 2-(hexadecyloxy)-, 1-(4-methylbenzenesulfonate)；2-hexadecoxyethyl 4-methylbenzenesulfonate
• CAS: 171364-92-4
• 化学式: C₂₅H₄₄O₄S
• 分子量: 440.688
• InChiKey: OGURYWDXBSXXLQ-UHFFFAOYSA-N

物化性质

• 沸点：
  535.8±33.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  30
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid 2-hexadecyloxy-ethyl ester 在 palladium on activated charcoal 吡啶 、 氢气 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 61.0h， 生成 Toluene-4-sulfonic acid 2,3-bis-(2-hexadecyloxy-ethoxy)-propyl ester
  参考文献：
  名称：

  Synthesis of novel cationic lipids with oxyethylene spacers at the linkages between hydrocarbon chains and pseudoglyceryl backbone

  摘要：

  Four novel cationic lipids with oligo-oxyethylene units at various linkage regions between the pseudoglyceryl backbone and the hydrocarbon chains have been synthesized. The membrane-forming properties of these new lipids are briefly presented. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01683-4
• 作为产物：
  描述：

  α-氢化-ω-羟基异十六烷醇聚(氧-1,2-乙烷二基) 、 对甲苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到Toluene-4-sulfonic acid 2-hexadecyloxy-ethyl ester
  参考文献：
  名称：

  Synthesis of novel cationic lipids with oxyethylene spacers at the linkages between hydrocarbon chains and pseudoglyceryl backbone

  摘要：

  Four novel cationic lipids with oligo-oxyethylene units at various linkage regions between the pseudoglyceryl backbone and the hydrocarbon chains have been synthesized. The membrane-forming properties of these new lipids are briefly presented. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01683-4

文献信息

• [EN] DI- AND TRI-CATIONIC GLYCOSYLATED ANTITUMOR ETHER LIPIDS, L-GUCOSYLATED GAELS AND RHAMNOSE-LINKED GAELS AS CYTOTOXIC AGENTS AGAINST EPITHELIAL CANCER CELLS AND CANCER STEM CELLS<br/>[FR] ETHERS LIPIDIQUES ANTITUMORAUX GLYCOSYLÉS DI- ET TRICATIONIQUES, GAEL L-GLYCOSYLÉS ET GAEL LIÉS À DU RHAMNOSE UTILISABLES EN TANT QU'AGENTS CYTOTOXIQUES DIRIGÉS CONTRE DES CELLULES ÉPITHÉLIALES CANCÉREUSES ET DES CELLULES SOUCHES CANCÉREUSES
  申请人：UNIV MANITOBA

  公开号：WO2015179983A1

  公开（公告）日：2015-12-03

  Glycosylated Antitumor Ether Lipids (GAELs) kill cancer cells by a nonapoptotic pathway which is an attractive strategy to avoid resistance. To further optimize the antitumor effect, we prepared various analogs of di-, and tri-cationic GAEL analogs differing in the nature of the sugar (D-giucose or L-glucose), the anomeric linkage as well as position of the glycerolipid moiety. The di- and tri-cationic GAELs were synthesized and their in vitro anticancer properties were evaluated against drug resistant and aggressively growing cancer cell lines derived from human breast, prostate, pancreatic and ovarian cancers. The most potent dicationic GAEL analogs were also studied against cancer stem cells obtained from breast BT 474, prostate DU145 and ovarian A2780cp cell lines. Our results indicate that the number of positive charges, the position of the amino substituents and the nature of the sugar have significant effects on the anticancer activities of these compounds. The most active analog kill 50% of the cells at concentration range of 0.5-5μΜ and 90% of the cells at the concentration of 1-10μΜ depending on type of cancer cells.

  糖基化抗肿瘤醚脂质（GAELs）通过一种非凋亡途径杀灭癌细胞，这是一种吸引人的策略，可以避免抗药性。为了进一步优化抗肿瘤效果，我们制备了不同的双-和三-阳离子GAEL类似物，其糖的性质（D-葡萄糖或L-葡萄糖）、缩醛键以及甘油脂类团的位置不同。合成了双-和三-阳离子GAEL类似物，并评估了它们对人类乳腺、前列腺、胰腺和卵巢癌衍生的耐药和快速生长的癌细胞系的体外抗癌性能。最有效的双阳离子GAEL类似物也针对从乳腺BT 474、前列腺DU145和卵巢A2780cp细胞系中获得的癌干细胞进行了研究。我们的结果表明，阳离子数量、氨基取代物的位置和糖的性质对这些化合物的抗癌活性有显著影响。最活跃的类似物在浓度范围为0.5-5μΜ时杀死50%的细胞，在浓度为1-10μΜ时杀死90%的细胞，具体取决于癌细胞类型。