(E)-4-(9-triphenylphosphoniumnonyloxy)stilbene iodide

• 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: (E)-4-(9-triphenylphosphoniumnonyloxy)stilbene iodide
• 英文别名: triphenyl-[9-[4-[(E)-2-phenylethenyl]phenoxy]nonyl]phosphanium;iodide
• 化学式: C₄₁H₄₄OP*I
• 分子量: 710.678
• InChiKey: BBQBTVXJWMOHMK-IRWWKPKRSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  44
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,9-二溴壬烷 在 sodium iodide 、 sodium hydroxide 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 6.5h， 生成 (E)-4-(9-triphenylphosphoniumnonyloxy)stilbene iodide
  参考文献：
  名称：

  Potent Antiglioblastoma Agents by Hybridizing the Onium-Alkyloxy-Stilbene Based Structures of an α7-nAChR, α9-nAChR Antagonist and of a Pro-Oxidant Mitocan

  摘要：

  Adenocarcinoma and glioblastoma cell lines express alpha 7- and alpha 9 alpha 10-containing nicotinic acetylcholine receptors (nAChRs), whose activation promotes tumor cell growth. On these cells, the triethylammoniumethyl ether of 4-stilbenol MG624, a known selective antagonist of alpha 7 and alpha 9 alpha 10 nAChRs, has antiproliferative activity. The structural analogy of MG624 with the mitocan RDM-4'BTPI, triphenylphosphoniumbutyl ether of pterostilbene, suggested us that molecular hybridization among their three substructures (stilbenoxy residue, alkylene linker, and terminal onium) and elongation of the alkylene linker might result in novel antitumor agents with higher potency and selectivity. We found that lengthening the ethylene bridge in the triethylammonium derivatives results in more potent and selective toxicity toward adenocarcinoma and glioblastoma cells, which was paralleled by increased alpha 7 and alpha 9 alpha 10 nAChR antagonism and improved ability of reducing mitochondrial ATP production. Elongation of the alkylene linker was advantageous also for the triphenylphosphonium derivatives resulting in a generalized enhancement of antitumor activity, associated with increased mitotoxicity.

  DOI：

  10.1021/acs.jmedchem.8b01052