5-(4-chloro-2-(2-fluorophenoxy)benzyl)-2H-1,2,4-triazole-3(4H)-thione | 1580001-11-1

• 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: 5-(4-chloro-2-(2-fluorophenoxy)benzyl)-2H-1,2,4-triazole-3(4H)-thione
• 英文别名: 5-[[4-Chloro-2-(2-fluorophenoxy)phenyl]methyl]-1,2-dihydro-1,2,4-triazole-3-thione；5-[[4-chloro-2-(2-fluorophenoxy)phenyl]methyl]-1,2-dihydro-1,2,4-triazole-3-thione
• CAS: 1580001-11-1
• 化学式: C₁₅H₁₁ClFN₃OS
• 分子量: 335.789
• InChiKey: DDQLLUDTVFNFMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  77.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-chloro-2-(2-fluorophenoxy)benzyl)-2H-1,2,4-triazole-3(4H)-thione 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.08h， 以44%的产率得到5-(4-chloro-2-(2-fluorophenoxy)benzyl)-3-ethylthio-4H-1,2,4-triazole
  参考文献：
  名称：

  Synthesis, receptor affinity and effect on pentylenetetrazole-induced seizure threshold of novel benzodiazepine analogues: 3-Substituted 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles and 2-amino-5-(phenoxybenzyl)-1,3,4-oxadiazoles

  摘要：

  The new series of 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles, possessing C-3 thio, alkylthio and ethoxy substituents, and 2-amino-5-(2-phenoxybenzyl)-1,3,4-oxadiazoles were designed and synthesized as novel benzodiazepine analogues. Most of them revealed similar to superior binding affinity to the GABA(A)/benzodiazepine receptor complex, relative to diazepam as the reference drug. Among them, 5-(4-chloro-2-(2-fluorophenoxy) benzyl)-3-benzylthio-4H-1,2,4-triazole (8l) showed the highest affinity (IC50 = 0.892 nM) relative to diazepam (IC50 = 2.857 nM) and also showed the most increase in pentylen-etetrazole-induced seizure threshold relative to diazepam as the reference drug. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.041
• 作为产物：
  描述：

  ethyl 4-chloro-2-(2-fluorophenoxy)benzoate 在 吡啶 、 lithium aluminium tetrahydride 、 氯化亚砜 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 、 苯 为溶剂， 反应 59.0h， 生成 5-(4-chloro-2-(2-fluorophenoxy)benzyl)-2H-1,2,4-triazole-3(4H)-thione
  参考文献：
  名称：

  Synthesis, receptor affinity and effect on pentylenetetrazole-induced seizure threshold of novel benzodiazepine analogues: 3-Substituted 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles and 2-amino-5-(phenoxybenzyl)-1,3,4-oxadiazoles

  摘要：

  The new series of 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles, possessing C-3 thio, alkylthio and ethoxy substituents, and 2-amino-5-(2-phenoxybenzyl)-1,3,4-oxadiazoles were designed and synthesized as novel benzodiazepine analogues. Most of them revealed similar to superior binding affinity to the GABA(A)/benzodiazepine receptor complex, relative to diazepam as the reference drug. Among them, 5-(4-chloro-2-(2-fluorophenoxy) benzyl)-3-benzylthio-4H-1,2,4-triazole (8l) showed the highest affinity (IC50 = 0.892 nM) relative to diazepam (IC50 = 2.857 nM) and also showed the most increase in pentylen-etetrazole-induced seizure threshold relative to diazepam as the reference drug. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.041