hexadecyl(2-hydroxybenzyl)diphenylphosphonium chloride

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: hexadecyl(2-hydroxybenzyl)diphenylphosphonium chloride
• 英文别名: Hexadecyl-[(2-hydroxyphenyl)methyl]-diphenylphosphanium;chloride；hexadecyl-[(2-hydroxyphenyl)methyl]-diphenylphosphanium;chloride
• 化学式: C₃₅H₅₀OP*Cl
• 分子量: 553.208
• InChiKey: NJWLFPGSOXIJQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.05
• 重原子数：
  38.0
• 可旋转键数：
  19.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  二苯基(2-羟基苯基甲基)膦氧化物 在 氯化亚砜 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 hexadecyl(2-hydroxybenzyl)diphenylphosphonium chloride
  参考文献：
  名称：

  Design and synthesis of amphiphilic 2-hydroxybenzylphosphonium salts with antimicrobial and antitumor dual action

  摘要：

  Here we report the synthesis and biological evaluation of a series of new 2-hydroxybenzylphosphonium salts (QPS) with antimicrobial and antitumor dual action. The most active compounds exhibit antimicrobial activity at a micromolar level against Gram-positive bacteria Sa (ATCC 209p and clinical isolates), Bc (1-2 mu M) and fungi Tm and Ca, and induced no notable hemolysis at MIC. The change in nature of substituents of the same length led to a drastic change of biological activity. Self-assembly behavior of the octadecyl and oleyl derivatives was studied. QPS demonstrated self-assembly within the micromolar range with the formation of nanosized aggregates capable of the solubilizing hydrophobic probe. The synthesized phosphonium salts were tested for cytotoxicity. The most potent salt was active against on M - Hela cell line with IC50 on the level of doxorubicin and good selectivity. According to the cytofluorimetry analysis, the salts induced mitochondria-dependent apoptosis.

  DOI：

  10.1016/j.bmcl.2020.127234