Trimethyl-(4-vinyl-phenyl)-ammonium; iodide | 82793-22-4

• 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: Trimethyl-(4-vinyl-phenyl)-ammonium; iodide
• 英文别名: 4-Ethenyl-N,N,N-trimethylanilinium iodide；(4-ethenylphenyl)-trimethylazanium;iodide
• CAS: 82793-22-4
• 化学式: C₁₁H₁₆N*I
• 分子量: 289.159
• InChiKey: KCASHJXEJBFZPX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.47
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-chloro-1-(4-trimethylammoniumphenyl)ethylphosphonic acid iodide 以 phosphate buffer 、 二甲基亚砜 为溶剂， 生成 Trimethyl-(4-vinyl-phenyl)-ammonium; iodide
  参考文献：
  名称：

  Novel Irreversible Butyrylcholinesterase Inhibitors: 2-Chloro-1-(substituted-phenyl)ethylphosphonic Acids

  摘要：

  2-Chloroethylphosphonic acid (ethephon) as the dianion phosphorylates butyrylcholinesterase (BChE) at its active site. In contrast, the classical organophosphorus esterase inhibitors include substituted-phenyl dialkylphosphates (e.g., paraoxon) with electron-withdrawing aryl substituents. The chloroethyl and substituted-phenyl moieties are combined in this study as 2-chloro-1-(substituted-phenyl)ethylphosphonic acids (1) to define the structure-activity relationships and mechanism of BChE inhibition by ethephon and its analogues. Phenyl substituents considered are 3- and 4-nitro, 3- and 4-dimethylamino. and 3- and 4-trimethyl-ammonium. Phosphonic acids 1 were synthesized via the corresponding O,O-diethyl phosphonate precursors followed by deprotection with trimethylsilyl bromide. They decompose under basic conditions about 100-fold faster than ethephon to yield the corresponding styrene derivatives. Electron-withdrawing substituents on the phenyl ring decrease the hydrolysis rate while electron-donating substituents increase the rate. The 4-trimethylammonium analogue has the highest affinity (K-i = 180 muM) and potency (IC50 = 19 muM) in first binding reversibly at the substrate site (possibly with stabilization in a dianion-monoanion environment) and then progressively and irreversibly inhibiting the enzyme activity. These observations suggest dissociation of chloride as the first and rate-limiting step both in the hydrolysis and by analogy in phosphorylation of BChE by 1 bound at the active site. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00391-1

文献信息

• Novel Irreversible Butyrylcholinesterase Inhibitors: 2-Chloro-1-(substituted-phenyl)ethylphosphonic Acids
  作者：Nanjing Zhang、John E Casida

  DOI：10.1016/s0968-0896(01)00391-1

  日期：2002.5

  2-Chloroethylphosphonic acid (ethephon) as the dianion phosphorylates butyrylcholinesterase (BChE) at its active site. In contrast, the classical organophosphorus esterase inhibitors include substituted-phenyl dialkylphosphates (e.g., paraoxon) with electron-withdrawing aryl substituents. The chloroethyl and substituted-phenyl moieties are combined in this study as 2-chloro-1-(substituted-phenyl)ethylphosphonic acids (1) to define the structure-activity relationships and mechanism of BChE inhibition by ethephon and its analogues. Phenyl substituents considered are 3- and 4-nitro, 3- and 4-dimethylamino. and 3- and 4-trimethyl-ammonium. Phosphonic acids 1 were synthesized via the corresponding O,O-diethyl phosphonate precursors followed by deprotection with trimethylsilyl bromide. They decompose under basic conditions about 100-fold faster than ethephon to yield the corresponding styrene derivatives. Electron-withdrawing substituents on the phenyl ring decrease the hydrolysis rate while electron-donating substituents increase the rate. The 4-trimethylammonium analogue has the highest affinity (K-i = 180 muM) and potency (IC50 = 19 muM) in first binding reversibly at the substrate site (possibly with stabilization in a dianion-monoanion environment) and then progressively and irreversibly inhibiting the enzyme activity. These observations suggest dissociation of chloride as the first and rate-limiting step both in the hydrolysis and by analogy in phosphorylation of BChE by 1 bound at the active site. (C) 2002 Elsevier Science Ltd. All rights reserved.