4-benzyl-5-(4-nitrophenyl)-4H-1,2,4-triazole-3-thiol | 23289-14-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-benzyl-5-(4-nitrophenyl)-4H-1,2,4-triazole-3-thiol
• 英文别名: 5-(4-Nitro-phenyl)-4-benzyl-3-mercapto-4H-1.2.4-triazol；4-benzyl-5-(4-nitro-phenyl)-2,4-dihydro-[1,2,4]triazole-3-thione；4-benzyl-3-(4-nitrophenyl)-1H-1,2,4-triazole-5-thione
• CAS: 23289-14-7
• 化学式: C₁₅H₁₂N₄O₂S
• mdl: MFCD01829302
• 分子量: 312.352
• InChiKey: FNPPASJCBXHHNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-二硝基苄氯 、 4-benzyl-5-(4-nitrophenyl)-4H-1,2,4-triazole-3-thiol 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以89%的产率得到4-benzyl-3-[(3,5-dinitrobenzyl)sulfanyl]-5-(4-nitrophenyl)-4H-1,2,4-triazole
  参考文献：
  名称：

  Development of 3,5-Dinitrophenyl-Containing 1,2,4-Triazoles and Their Trifluoromethyl Analogues as Highly Efficient Antitubercular Agents Inhibiting Decaprenylphosphoryl-β-d-ribofuranose 2′-Oxidase

  摘要：

  We report herein the discovery of 3,5-dinitrophenyl 1,2,4-triazoles with excellent and selective antimycobacterial activities against Mycobacterium tuberculosis strains, including clinically isolated multidrug-resistant strains. Thorough structure activity relationship studies of 3,5-dinitrophenyl-containing 1,2,4-triazoles and their trifluoromethyl analogues revealed the key role of the position of the 3,5-dinitrophenyl fragment in the antitubercular efficiency. Among the prepared compounds, the highest in vitro antimycobacterial activities against M. tuberculosis H(37)Rv and against seven clinically isolated multidrug-resistant strains of M. tuberculosis were found with S-substituted 4-alkyl-5-(3,5-dinitrophenyl)-4H-1,2,4-triazole-3-thiols and their 3-nitro-5-(trifluoromethyl)phenyl analogues. The minimum inhibitory concentrations of these compounds reached 0.03 mu M, which is superior to all the current first-line anti-tuberculosis drugs. Furthermore, almost all compounds with excellent antimycobacterial activities exhibited very low in vitro cytotoxicities against two proliferating mammalian cell lines. The docking study indicated that these compounds acted as the inhibitors of decaprenylphosphoryl-beta-D-ribofuranose 2'-oxidase enzyme, which was experimentally confirmed by two independent radiolabeling experiments.

  DOI：

  10.1021/acs.jmedchem.9b00912
• 作为产物：
  描述：

  4-benzyl-1-(4-nitrobenzoyl)thiosemicarbazide 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 4.0h， 以75%的产率得到4-benzyl-5-(4-nitrophenyl)-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  Development of 3,5-Dinitrophenyl-Containing 1,2,4-Triazoles and Their Trifluoromethyl Analogues as Highly Efficient Antitubercular Agents Inhibiting Decaprenylphosphoryl-β-d-ribofuranose 2′-Oxidase

  摘要：

  We report herein the discovery of 3,5-dinitrophenyl 1,2,4-triazoles with excellent and selective antimycobacterial activities against Mycobacterium tuberculosis strains, including clinically isolated multidrug-resistant strains. Thorough structure activity relationship studies of 3,5-dinitrophenyl-containing 1,2,4-triazoles and their trifluoromethyl analogues revealed the key role of the position of the 3,5-dinitrophenyl fragment in the antitubercular efficiency. Among the prepared compounds, the highest in vitro antimycobacterial activities against M. tuberculosis H(37)Rv and against seven clinically isolated multidrug-resistant strains of M. tuberculosis were found with S-substituted 4-alkyl-5-(3,5-dinitrophenyl)-4H-1,2,4-triazole-3-thiols and their 3-nitro-5-(trifluoromethyl)phenyl analogues. The minimum inhibitory concentrations of these compounds reached 0.03 mu M, which is superior to all the current first-line anti-tuberculosis drugs. Furthermore, almost all compounds with excellent antimycobacterial activities exhibited very low in vitro cytotoxicities against two proliferating mammalian cell lines. The docking study indicated that these compounds acted as the inhibitors of decaprenylphosphoryl-beta-D-ribofuranose 2'-oxidase enzyme, which was experimentally confirmed by two independent radiolabeling experiments.

  DOI：

  10.1021/acs.jmedchem.9b00912