5-(2-phenoxybenzyl)-2H-1,2,4-triazole-3(4H)-thione | 1580001-09-7

• 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-(2-phenoxybenzyl)-2H-1,2,4-triazole-3(4H)-thione
• 英文别名: 5-[(2-Phenoxyphenyl)methyl]-1,2-dihydro-1,2,4-triazole-3-thione；5-[(2-phenoxyphenyl)methyl]-1,2-dihydro-1,2,4-triazole-3-thione
• CAS: 1580001-09-7
• 化学式: C₁₅H₁₃N₃OS
• 分子量: 283.354
• InChiKey: BYHKQDAEDFUGSN-UHFFFAOYSA-N

物化性质

• 熔点：
  217-219 °C
• 沸点：
  404.5±55.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 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：
  2

反应信息

• 作为反应物：
  描述：

  5-(2-phenoxybenzyl)-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80%的产率得到5-(2-phenoxybenzyl)-3-methylthio-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：

  苯氧苯甲酸 在 吡啶 、 lithium aluminium tetrahydride 、 氯化亚砜 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二甲基亚砜 、 正丁醇 、 苯 为溶剂， 反应 63.0h， 生成 5-(2-phenoxybenzyl)-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

文献信息

• 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
  作者：Siavash Mashayekh、Narges Rahmanipour、Behnaz Mahmoodi、Fatemeh Ahmadi、Dina Motaharian、Soraya Shahhosseini、Hamed Shafaroodi、Hamid R. Banafshe、Abbas Shafiee、Latifeh Navidpour

  DOI：10.1016/j.bmc.2014.01.041

  日期：2014.3

  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.