1-(4-chlorophenyl)-4-((5-mercapto-1,3,4-thiadiazol-2-yl)methyl)-1,4-dihydro-5H-tetrazol-5-one | 928343-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-chlorophenyl)-4-((5-mercapto-1,3,4-thiadiazol-2-yl)methyl)-1,4-dihydro-5H-tetrazol-5-one
• CAS: 928343-00-4
• 化学式: C₁₀H₇ClN₆OS₂
• 分子量: 326.79
• InChiKey: KEACZFFLTIFEQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  78.49
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-4-((5-mercapto-1,3,4-thiadiazol-2-yl)methyl)-1,4-dihydro-5H-tetrazol-5-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以74%的产率得到1-[(5-Benzylsulfanyl-1,3,4-thiadiazol-2-yl)methyl]-4-(4-chlorophenyl)tetrazol-5-one
  参考文献：
  名称：

  Discovery of a new insecticide lead by optimizing a target-diverse scaffold: Tetrazolinone derivatives

  摘要：

  In order to discover lead compounds with novel action mechanism, a series of tetrazolinone derivatives bearing structurally diverse substituents, 1-aryl-4-substituted-1,4-di-hydro-5H-tetrazol-5-ones 2, 1-((5-(alkylthio)-1,3,4-oxadiazol-2-yl)methyl)-4-(substituted)- phenyl-1H-tetrazol-5(4H)-ones 5, and 1-((5-(alkylthio)-1,3,4-thiadiazol-2-yl)methyl)-4-(substituted)phenyl-1H-tetrazol5(4H)-ones 7, were designed and synthesized in good yields by a multiple-step synthetic procedure. The results of greenhouse in vivo test indicated that all the target compounds did not displayed herbicidal activity, however, some of them exhibited excellent in vivo insecticidal activity against Tetranychus cinnabarinus at the concentration of 250 mg L-1. To our knowledge, this is the first report about the insecticidal activity of tetrazolinone derivatives, which indicated that the tetrazolinone scaffold could be identified as a novel insecticidal lead structure. The present work demonstrated that optimizing a target-diverse scaffold is an effective way to discover new lead compounds with new action mechanism or biological activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.002
• 作为产物：
  描述：

  二硫化碳 、 2-[4-(4-chlorophenyl)-5-oxo-1,4-dihydro-5H-tetrazol-1-yl]acetohydrazide 在 氢氧化钾 、 硫酸 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以84%的产率得到1-(4-chlorophenyl)-4-((5-mercapto-1,3,4-thiadiazol-2-yl)methyl)-1,4-dihydro-5H-tetrazol-5-one
  参考文献：
  名称：

  Discovery of a new insecticide lead by optimizing a target-diverse scaffold: Tetrazolinone derivatives

  摘要：

  In order to discover lead compounds with novel action mechanism, a series of tetrazolinone derivatives bearing structurally diverse substituents, 1-aryl-4-substituted-1,4-di-hydro-5H-tetrazol-5-ones 2, 1-((5-(alkylthio)-1,3,4-oxadiazol-2-yl)methyl)-4-(substituted)- phenyl-1H-tetrazol-5(4H)-ones 5, and 1-((5-(alkylthio)-1,3,4-thiadiazol-2-yl)methyl)-4-(substituted)phenyl-1H-tetrazol5(4H)-ones 7, were designed and synthesized in good yields by a multiple-step synthetic procedure. The results of greenhouse in vivo test indicated that all the target compounds did not displayed herbicidal activity, however, some of them exhibited excellent in vivo insecticidal activity against Tetranychus cinnabarinus at the concentration of 250 mg L-1. To our knowledge, this is the first report about the insecticidal activity of tetrazolinone derivatives, which indicated that the tetrazolinone scaffold could be identified as a novel insecticidal lead structure. The present work demonstrated that optimizing a target-diverse scaffold is an effective way to discover new lead compounds with new action mechanism or biological activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.002