4-(4-chlorophenyl)-5-(2-hydroxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione | 26131-65-7

• 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-(4-chlorophenyl)-5-(2-hydroxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
• 英文别名: 4-(4-Chlorophenyl)-2,4-dihydro-5-(2-hydroxyphenyl)-3H-1,2,4-triazole-3-thione；4-(4-chlorophenyl)-3-(2-hydroxyphenyl)-1H-1,2,4-triazole-5-thione
• CAS: 26131-65-7
• 化学式: C₁₄H₁₀ClN₃OS
• 分子量: 303.772
• InChiKey: YDJNLGINEGIEIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.84
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 4-(4-chlorophenyl)-5-(2-hydroxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 、 环丙沙星 以 乙醇 为溶剂， 反应 12.0h， 以75%的产率得到1-cyclopropyl-6-fluoro-7-[4-{[4-(4-chlorophenyl)-3-(2-hydroxyphenyl)-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}piperazin-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Search for factors affecting antibacterial activity and toxicity of 1,2,4-triazole-ciprofloxacin hybrids

  摘要：

  A series of 1,2,4-triazole-based compounds was designed as potential antibacterial agents using molecular hybridization approach. The target compounds (23-44) were synthesized by Mannich reaction of 1,2,4-triazole-3-thione derivatives with ciprofloxacin (CPX) and formaldehyde. Their potent antibacterial effect on Gram-positive bacteria was accompanied by similarly strong activity against Gram-negative strains. The toxicity of the CPX-triazole hybrids for bacterial cells was even up to 18930 times higher than the toxicity for human cells. The results of enzymatic studies showed that the antibacterial activity of the CPX-triazole hybrids is not dependent solely on the degree of their affinity to DNA gyrase and topoisomerase IV. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.058
• 作为产物：
  描述：

  4-(4-氯苯基)-1-(2-羟基苯甲酰基)氨基硫脲 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以87%的产率得到4-(4-chlorophenyl)-5-(2-hydroxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  Search for factors affecting antibacterial activity and toxicity of 1,2,4-triazole-ciprofloxacin hybrids

  摘要：

  A series of 1,2,4-triazole-based compounds was designed as potential antibacterial agents using molecular hybridization approach. The target compounds (23-44) were synthesized by Mannich reaction of 1,2,4-triazole-3-thione derivatives with ciprofloxacin (CPX) and formaldehyde. Their potent antibacterial effect on Gram-positive bacteria was accompanied by similarly strong activity against Gram-negative strains. The toxicity of the CPX-triazole hybrids for bacterial cells was even up to 18930 times higher than the toxicity for human cells. The results of enzymatic studies showed that the antibacterial activity of the CPX-triazole hybrids is not dependent solely on the degree of their affinity to DNA gyrase and topoisomerase IV. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.058