4-bromo-2-[(3,4-dichlorophenyl)carbamoyl]phenyl diethyl phosphate | 1552270-20-8

• 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: 4-bromo-2-[(3,4-dichlorophenyl)carbamoyl]phenyl diethyl phosphate
• 英文别名: [4-Bromo-2-[(3,4-dichlorophenyl)carbamoyl]phenyl] diethyl phosphate；[4-bromo-2-[(3,4-dichlorophenyl)carbamoyl]phenyl] diethyl phosphate
• CAS: 1552270-20-8
• 化学式: C₁₇H₁₇BrCl₂NO₅P
• 分子量: 497.109
• InChiKey: VTOUJCOSUXDNJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-溴-N-(3,4-二氯苯基)-2-羟基苯甲酰胺 、 氯磷酸二乙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.08h， 以73%的产率得到4-bromo-2-[(3,4-dichlorophenyl)carbamoyl]phenyl diethyl phosphate
  参考文献：
  名称：

  水杨酰苯胺二乙基磷酸酯：合成，抗菌活性和细胞毒性

  摘要：

  作为我们持续寻找新的抗菌活性药物的一部分，制备了一系列27种水杨酰苯胺二乙基磷酸酯。所有化合物均具有针对结核分枝杆菌，堪萨斯分枝杆菌和鸟分枝杆菌菌株的体外活性，最低抑菌浓度（MIC）值为0.5–62.5μmol/ L。选定的水杨酰苯胺二乙基磷酸酯还可以以1μmol/ L的浓度抑制耐多药结核病菌株。水杨酰苯胺二乙基磷酸酯也主要表现出对革兰氏阳性细菌的活性（MIC⩾1.95μmol/ L），而其抗真菌活性却明显较低。IC 50 Hep G2细胞的MCI值在1.56-33.82μmol/ L的范围内，但与分枝杆菌的MIC并没有直接相关性。

  DOI：

  10.1016/j.bmc.2013.12.016

文献信息

• Salicylanilide diethyl phosphates as cholinesterases inhibitors
  作者：Martin Krátký、Šárka Štěpánková、Katarína Vorčáková、Jarmila Vinšová

  DOI：10.1016/j.bioorg.2014.11.005

  日期：2015.2

  Based on the presence of dialkyl phosphate moiety, we evaluated twenty-seven salicylanilide diethyl phosphates (diethyl [2-(phenylcarbamoyl) phenyl] phosphates) for the inhibition of acetylcholinesterase (AChE) from electric eel (Electrophorus electricus L.) and butyrylcholinesterase (BChE) from equine serum. Ellman's spectrophotometric method was used. The inhibitory activity (expressed as IC50 values) was compared with that of the established drugs galantamine and rivastigmine. Salicylanilide diethyl phosphates showed significant activity against both cholinesterases with IC50 values from 0.903 to 86.3 mu M. IC(50)s for BChE were comparatively lower than those obtained for AChE. All of the investigated compounds showed higher inhibition of AChE than rivastigmine, and six of them inhibited BChE more effectively than both rivastigmine and galantamine. In general, derivatives of 4-chlorosalicylic acid showed enhanced activity when compared to derivatives of 5-halogenated salicylic acids, especially against BChE. The most effective inhibitor of AChE was O-5-chloro-2-[(3-bromophenyl) carbamoyl] phenyl} O, O-diethyl phosphate with IC50 of 35.4 mu M, which is also one of the most potent inhibitors of BChE. O-5-Chloro-2-[( 3,4-dichlorophenyl) carbamoyl] phenyl} O, O-diethyl phosphate exhibited in vitro the strongest inhibition of BChE (0.90 mu M). Salicylanilide diethyl phosphates act as pseudo-irreversible cholinesterases inhibitors. (C) 2014 Elsevier Inc. All rights reserved.