5-(1-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidin-2-ylthio)ethyl)-1,3,4-oxadiazole-2-thiol | 1022914-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 5-(1-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidin-2-ylthio)ethyl)-1,3,4-oxadiazole-2-thiol
• CAS: 1022914-15-3
• 化学式: C₁₁H₁₂N₆OS₂
• 分子量: 308.388
• InChiKey: XBIFWTGJCUIOMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 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：
  0.36
• 拓扑面积：
  82.0
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5-(1-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidin-2-ylthio)ethyl)-1,3,4-oxadiazole-2-thiol 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以80%的产率得到2-[1-[(5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfanyl]ethyl]-5-[(2-fluorophenyl)methylsulfanyl]-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis, antifungal activity and CoMFA analysis of novel 1,2,4-triazolo[1,5-a]pyrimidine derivatives

  摘要：

  In order to search novel agrochemicals with higher antifungal activity, a series of new 1,2,4-triazolo[1,5-a]pyrimidine derivatives bearing 1,3,4-oxadiazole moieties were designed and synthesized. Their antifungal activities against Rhizoctonia solani were evaluated in vitro. By determining the EC50 values of all the newly synthesized compounds and 10 formerly synthesized compounds, compound 8r, 2-((5-(sec-butylthio)1,3,4-oxadiazol-2-yl)-methylthio)-5-dimethyl-1,2,4-triazolo-[1,5-a]pyrimidine, was found to display the highest antifungal activity (EC50 = 6.57 mu g mL(-1)). Based on the quantitative structure-activity relationships analyses, 2-(1-(5-(sec-butylthio)- 1,3,4-oxadiazol-2-yl)ethylthio)-5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine (9j) was designed and synthesized, which was found to display much higher activity (EC50 = 3.34 mu g mL(-1)) than compound 8r and the control. To further explore the comprehensive structure-activity relationships, a 3D-QSAR analysis using the method of comparative molecular field analysis (CoMFA) was performed and a statistically reliable model with good predictive power (r(2) = 0.929, q(2) = 0.588) was achieved on the basis of the common substructure-based alignment. According to the CoMFA model, the structure-antifungal activity relationship was explained reasonably. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.04.021
• 作为产物：
  描述：

  二硫化碳 、 2-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidin-2-ylthio)propionic acid hydrazide 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以81%的产率得到5-(1-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidin-2-ylthio)ethyl)-1,3,4-oxadiazole-2-thiol
  参考文献：
  名称：

  Synthesis, antifungal activity and CoMFA analysis of novel 1,2,4-triazolo[1,5-a]pyrimidine derivatives

  摘要：

  In order to search novel agrochemicals with higher antifungal activity, a series of new 1,2,4-triazolo[1,5-a]pyrimidine derivatives bearing 1,3,4-oxadiazole moieties were designed and synthesized. Their antifungal activities against Rhizoctonia solani were evaluated in vitro. By determining the EC50 values of all the newly synthesized compounds and 10 formerly synthesized compounds, compound 8r, 2-((5-(sec-butylthio)1,3,4-oxadiazol-2-yl)-methylthio)-5-dimethyl-1,2,4-triazolo-[1,5-a]pyrimidine, was found to display the highest antifungal activity (EC50 = 6.57 mu g mL(-1)). Based on the quantitative structure-activity relationships analyses, 2-(1-(5-(sec-butylthio)- 1,3,4-oxadiazol-2-yl)ethylthio)-5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine (9j) was designed and synthesized, which was found to display much higher activity (EC50 = 3.34 mu g mL(-1)) than compound 8r and the control. To further explore the comprehensive structure-activity relationships, a 3D-QSAR analysis using the method of comparative molecular field analysis (CoMFA) was performed and a statistically reliable model with good predictive power (r(2) = 0.929, q(2) = 0.588) was achieved on the basis of the common substructure-based alignment. According to the CoMFA model, the structure-antifungal activity relationship was explained reasonably. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.04.021