4-(2-hydroxy-5-brominebenzylideneamino)-3-(2-hydroxyphenyl)-1,2,4–triazole-5-thione | 1428325-19-2

• 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-(2-hydroxy-5-brominebenzylideneamino)-3-(2-hydroxyphenyl)-1,2,4–triazole-5-thione
• 英文别名: 4-(2-hydroxy-5-brominebenzylideneamino)-3-(2-hydroxyphenyl)-1,2,4-triazole-5-thione
• CAS: 1428325-19-2
• 化学式: C₁₅H₁₁BrN₄O₂S
• 分子量: 391.248
• InChiKey: SMOZMYWYYSEDSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.43
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(2-hydroxy-5-brominebenzylideneamino)-3-(2-hydroxyphenyl)-1,2,4–triazole-5-thione 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 potassium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 8.0h， 以63%的产率得到
  参考文献：
  名称：

  Efficient synthesis and antimicrobial activity of some novel S-β-d-glucosides of 5-aryl-1,2,4-triazole-3-thiones derivatives

  摘要：

  A series of 3-S-beta-D-glucosides-4-arylideneamino-5-aryl-1,2,4-triazoles were rationally designed and synthesized according to the principle of superposition of bioactive substructures by the combination of 1,2,4-triazole, Schiff base and glucosides. The structures of the target compounds have been characterized by H-1 NMR, C-13 NMR, IR, MS and HRMS. All the newly synthesized compounds have been evaluated for their antimicrobial activities in vitro against Staphylococcus aureus (ATCC 6538), Escherichia coli (ATCC 8099) as well as Monilia albican (ATCC 10231). The bioactive assay showed that most of the tested compounds displayed variable inhibitory effects on the growth of the Gram-positive bacterial strain (Staphylococcus aureus), Gram-negative bacterial strains (Escherichia coli) and fungal strains (Monilia albican). All the target compounds exhibited better antifungal activity than antibacterial activity. Especially, compounds 6b, 6c, 6f, 6j, 6k and 6l showed excellent activity against fungus Monilia albican with MIC values of 16 mu g/mL. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.038
• 作为产物：
  描述：

  水杨酸甲酯 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 4-(2-hydroxy-5-brominebenzylideneamino)-3-(2-hydroxyphenyl)-1,2,4–triazole-5-thione
  参考文献：
  名称：

  Efficient synthesis and antimicrobial activity of some novel S-β-d-glucosides of 5-aryl-1,2,4-triazole-3-thiones derivatives

  摘要：

  A series of 3-S-beta-D-glucosides-4-arylideneamino-5-aryl-1,2,4-triazoles were rationally designed and synthesized according to the principle of superposition of bioactive substructures by the combination of 1,2,4-triazole, Schiff base and glucosides. The structures of the target compounds have been characterized by H-1 NMR, C-13 NMR, IR, MS and HRMS. All the newly synthesized compounds have been evaluated for their antimicrobial activities in vitro against Staphylococcus aureus (ATCC 6538), Escherichia coli (ATCC 8099) as well as Monilia albican (ATCC 10231). The bioactive assay showed that most of the tested compounds displayed variable inhibitory effects on the growth of the Gram-positive bacterial strain (Staphylococcus aureus), Gram-negative bacterial strains (Escherichia coli) and fungal strains (Monilia albican). All the target compounds exhibited better antifungal activity than antibacterial activity. Especially, compounds 6b, 6c, 6f, 6j, 6k and 6l showed excellent activity against fungus Monilia albican with MIC values of 16 mu g/mL. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.038