5-(4-nitrophenyl)-4-(p-tolyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-nitrophenyl)-4-(p-tolyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
• 英文别名: 5-(4-Nitro-phenyl)-4-p-tolyl-4H-[1,2,4]triazole-3-thiol；4-(4-methylphenyl)-3-(4-nitrophenyl)-1H-1,2,4-triazole-5-thione
• 化学式: C₁₅H₁₂N₄O₂S
• 分子量: 312.352
• InChiKey: FAQKMUFCAMKSMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-硝基苯酰肼 、 对甲苯异硫氰酸酯 以 甘油 为溶剂， 以88%的产率得到5-(4-nitrophenyl)-4-(p-tolyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  Synthesis, antimicrobial and antioxidant evaluation, and molecular docking study of 4,5-disubstituted 1,2,4-triazole-3-thiones

  摘要：

  There is a growing need for new antibiotics and antifungal drugs to combat pathogenic bacteria and fungi. In order to develop potential antimicrobial agents, some 1,2,4-triazole-3-thiones were synthesized from the reaction of hydrazides with isothiocyanates under optimized conditions in deep eutectic solvent of potassium carbonate-glycerol (1:5 M ratio). Blocking properties of all products were assessed on a variety of Gram-positive and Gram-negative bacterial as well as fungal pathogens. Good to excellent inhibitory effects especially against fungi were observed with all synthesized compounds. 5-(4-Hydroxyphenyl)-4-(4-nitrophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (3b) showed significant antioxidant activity according to the results obtained from 2,2-diphenyl-1-picrylhydrazylf (DPPH) free radical scavenging experiments. The possible interaction mechanism of synthetic triazoles with 1IYL enzyme on Aspergillus fumigatus was investigated by molecular docking method. A complete agreement was found between experimental data and theoretical calculations. Hydrogen bond acceptor strength of N-1 in 1,2,4-triazole rings was the main cause of the observed differences. (C) 2020 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2020.128273