ethyl-dimethyl-{2-[methyl-(tetradecane-1-sulfonyl)-amino]-ethyl}-ammonium iodide | 1174585-11-5

• 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: ethyl-dimethyl-{2-[methyl-(tetradecane-1-sulfonyl)-amino]-ethyl}-ammonium iodide
• 英文别名: Ethyl-dimethyl-[2-[methyl(tetradecylsulfonyl)amino]ethyl]azanium;iodide；ethyl-dimethyl-[2-[methyl(tetradecylsulfonyl)amino]ethyl]azanium;iodide
• CAS: 1174585-11-5
• 化学式: C₂₁H₄₇N₂O₂S*I
• 分子量: 518.587
• InChiKey: MVMKUYYIVIPZRR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  27
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  十四烷-1-磺化钠 在 氯化亚砜 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 ethyl-dimethyl-{2-[methyl-(tetradecane-1-sulfonyl)-amino]-ethyl}-ammonium iodide
  参考文献：
  名称：

  New synthetic aliphatic sulfonamido-quaternary ammonium salts as anticancer chemotherapeutic agents

  摘要：

  RhoB is expressed during tumor cell proliferation, survival, invasion, and metastasis. In malignant progression, the expression levels of RhoB are commonly attenuated. RhoB is known to be linked to the regulation of the PI3K/Akt survival pathways. Based on aliphatic amido-quaternary ammonium salts that induce apoptosis via up-regulation of RhoB, we synthesized novel aliphatic sulfonamido-quaternary ammonium salts. These new synthetic compounds were evaluated for their biological activities using an in vitro RhoB promoter assay in HeLa cells, and in a growth inhibition assay using human cancer cell lines including PC-3, NUGC-3, MDA-MB-231, ACHN, HCT-15, and NCI-H23. Compound 5b (ethyl-dimethyl-{3-[methyl-(tetradecane-1-sulfonyl)-amino]-propyl}-ammonium; iodide) was the most promising anticancer agent in the series, based upon the potency of growth inhibition and RhoB promotion. These new aliphatic sulfonamido-quaternary ammonium salts could be a valuable series for development of new anticancer chemotherapeutic agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.022

文献信息

• New synthetic aliphatic sulfonamido-quaternary ammonium salts as anticancer chemotherapeutic agents
  作者：Doona Song、Jee Sun Yang、Changmok Oh、Shuolin Cui、Bo-Kyung Kim、Misun Won、Jang-ik Lee、Hwan Mook Kim、Gyoonhee Han

  DOI：10.1016/j.ejmech.2013.09.022

  日期：2013.11

  RhoB is expressed during tumor cell proliferation, survival, invasion, and metastasis. In malignant progression, the expression levels of RhoB are commonly attenuated. RhoB is known to be linked to the regulation of the PI3K/Akt survival pathways. Based on aliphatic amido-quaternary ammonium salts that induce apoptosis via up-regulation of RhoB, we synthesized novel aliphatic sulfonamido-quaternary ammonium salts. These new synthetic compounds were evaluated for their biological activities using an in vitro RhoB promoter assay in HeLa cells, and in a growth inhibition assay using human cancer cell lines including PC-3, NUGC-3, MDA-MB-231, ACHN, HCT-15, and NCI-H23. Compound 5b (ethyl-dimethyl-3-[methyl-(tetradecane-1-sulfonyl)-amino]-propyl}-ammonium; iodide) was the most promising anticancer agent in the series, based upon the potency of growth inhibition and RhoB promotion. These new aliphatic sulfonamido-quaternary ammonium salts could be a valuable series for development of new anticancer chemotherapeutic agents. (C) 2013 Elsevier Masson SAS. All rights reserved.