2-甲基-5-苯基-2,4-二氢-[1,2,4]三唑-3-硫酮 | 39696-48-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-甲基-5-苯基-2,4-二氢-[1,2,4]三唑-3-硫酮
• 英文名称: 2-methyl-5-phenyl-2,4-dihydro-[1,2,4]triazole-3-thione
• 英文别名: 1-Methyl-3-phenyl-1,2,4-triazolin-5-thion；1-Methyl-3-phenyl-1,2,4-triazol-5-thion；2-methyl-5-phenyl-1H-1,2,4-triazole-3-thione
• CAS: 39696-48-5
• 化学式: C₉H₉N₃S
• 分子量: 191.257
• InChiKey: CBNSLHGHYGHNIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  265-267 °C
• 沸点：
  270.1±23.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-甲基-5-苯基-2,4-二氢-[1,2,4]三唑-3-硫酮 在 sodium hydroxide 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 1-甲基-5-甲基亚磺酰-3-苯基-1,2,4-三唑
  参考文献：
  名称：

  Kane; Staeger; Dalton, Journal of Medicinal Chemistry, 1994, vol. 37, # 1, p. 125 - 132

  摘要：

  DOI：
• 作为产物：
  描述：

  1-Benzoyl-2-methyl-thiosemicarbazid 在 碳酸氢钠 作用下， 生成 2-甲基-5-苯基-2,4-二氢-[1,2,4]三唑-3-硫酮
  参考文献：
  名称：

  Synthesis and structure—activity relationship of C-3 substituted triazolylthiomethyl cephems

  摘要：

  A series of C-3 substituted triazolylthiomethyl cephems with an aminothiazolemethoxyiminoacetamido side chain at C-7 were synthesized and tested for antimicrobial activity against clinically-relevant isolates. The compound with 3-pyridyl at C-5 and methyl at N-4 of the triazole moiety exhibited good antibacterial activity against both Gram-positive and Gram-negative bacteria, with the exception of pseudomonas spp against which none of the derivatives exhibited favorable activity.

  DOI：

  10.1016/0223-5234(96)80367-9

文献信息

• 2,4-Dihydro-3H-1,2,4-triazol-3-ones as anticonvulsant agents
  作者：John M. Kane、Bruce M. Baron、Mark W. Dudley、Stephen M. Sorensen、Michael A. Staeger、Francis P. Miller

  DOI：10.1021/jm00172a015

  日期：1990.10

  A series of 5-aryl-2,4-dihydro-3H-1,2,4-triazol-3-ones was evaluated for anticonvulsant activity. In general the members of this series were prepared by the alkaline cyclization of 1-aroyl-4-alkylsemicarbazides. The resulting 2-unsubstituted 3H-1,2,4-triazol-3-ones were then alkylated, yielding 2,4-dialkyl-3H-1,2,4-triazol-3-ones. Approximately one-third of the compounds examined exhibited activity against both maximal electroshock- and pentylenetetrazole-induced seizures in mice. Receptor-binding studies suggest that this activity was not a consequence of activity at either benzodiazepine or NMDA-type glutamate receptors. From this series, compound 45 was selected for further evaluation where it was also found to be active against 3-mercaptopropionic acid, bicuculline, and quinolinic acid induced seizures in mice. In addition, 45 also protected gerbils from hippocampal neuronal degeneration produced by either hypoxia or intrastriatal quinolinic acid injection.
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  作者：Hasnaoui, A.、Lavergne, J.-P.、Viallefont, Ph.

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