2-(ethylthio)-5-(4-methylphenyl)-1,3,4-oxadiazole | 1018204-23-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(ethylthio)-5-(4-methylphenyl)-1,3,4-oxadiazole
• 英文别名: 2-(ethylthio)-5-(p-tolyl)-1,3,4-oxadiazole；2-(Ethylsulfanyl)-5-(4-methylphenyl)-1,3,4-oxadiazole；2-ethylsulfanyl-5-(4-methylphenyl)-1,3,4-oxadiazole
• CAS: 1018204-23-3
• 化学式: C₁₁H₁₂N₂OS
• mdl: MFCD02278473
• 分子量: 220.295
• InChiKey: XUXNAUCHKKTXQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(ethylthio)-5-(4-methylphenyl)-1,3,4-oxadiazole 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium hydride 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 2-(ethylthio)-5-(4-((2-propynyloxy)methyl)phenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Sulfone-Based Probes Unraveled Dihydrolipoamide S-Succinyltransferase as an Unprecedented Target in Phytopathogens

  摘要：

  Target validation of current drugs remains the major challenge for target-based drug discovery, especially for agrochemical discovery. The bactericide 0 represents a novel lead structure and has shown potent efficacy against those diseases that are extremely difficult to control, such as rice bacterial leaf blight. However, no detailed target analysis of this bactericide has been reported. Here, we developed a panel of 0-derived probes 1-6, in which a conservative modification (alkyne tag) was introduced to keep the antibacterial activity of 0 and provide functionality for target identification via click chemistry. With these cell-permeable probes, we were able to discover dihydrolipoamide S-succinyltransferase (DLST) as an unprecedented target in living cells. The probes showed good preference for DLST, especially probe 1, which demonstrated distinct selectivity and reactivity. Also, we reported 0 as the first covalent DLST inhibitor, which has been used to confirm the involvement of DLST in the regulation of energy production.

  DOI：

  10.1021/acs.jafc.9b02059
• 作为产物：
  描述：

  对甲基苯甲酸甲酯 在 一水合肼 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 2-(ethylthio)-5-(4-methylphenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Inhibition of Tobacco Bacterial Wilt with Sulfone Derivatives Containing an 1,3,4-Oxadiazole Moiety

  摘要：

  A series of new sulfone compounds containing the 1,3,4-oxadiazole moiety were designed and synthesized. Their structures were identified by H-1 and C-13 nuclear magnetic resonance and elemental analyses. Antibacterial bioassays indicated that most compounds exhibited promising in vitro antibacterial bioactivities against tobacco bacterial wilt at 200 mu g/mL. The relationship between structure and antibacterial activity was also discussed. Among the title compounds, 5'c:, 5'h, 5'i, and 5, could inhibit mycelia growth of Ralstonia solanacearum in vitro by approximately 50% (EC50) at 39.8, 60.3, 47.9, and 32.1 mu g/mL, respectively. Among them, compound 5) was identified as the most promising candidate due to its stronger effect than that of Kocide 3000 [Cu(OH)(2)] within the same concentration range. Field trials demonstrated that the control effect of compound 55 against tobacco bacterial wilt was better than that of the commercial bactericide Saisentong. For the first time, the present work demonstrated that sulfone derivatives containing 1,3,4-oxadiazole can be used to develop potential bactericides for plants.

  DOI：

  10.1021/jf203772d

文献信息

• A novel one-pot synthesis of 2-alkylthio-1,3,4-oxadiazoles in water
  作者：F. Aryanasab、H. Maleki、M. R. Saidi

  DOI：10.1007/bf03249086

  日期：2011.6

  A facile and one-pot protocol for the synthesis of 2-alkylthio-1,3,4-oxadiazoles is reported. This green method relies on the reaction of acid hydrazides with CS2 and an alkyl halide. The reaction is carried out under mild and environmentally friendly procedure in water with high to excellent yields. Thirteen different valuable alkylthio-1,3,4-oxadiazoles are synthesized from cheap and easily available CS2 with this method. This is the first report for the synthesis of 1,3,4-oxadiazoles in water.
• Inhibition of Tobacco Bacterial Wilt with Sulfone Derivatives Containing an 1,3,4-Oxadiazole Moiety
  作者：Wei-Ming Xu、Fei-Fei Han、Ming He、De-Yu Hu、Jiang He、Song Yang、Bao-An Song

  DOI：10.1021/jf203772d

  日期：2012.2.1

  A series of new sulfone compounds containing the 1,3,4-oxadiazole moiety were designed and synthesized. Their structures were identified by H-1 and C-13 nuclear magnetic resonance and elemental analyses. Antibacterial bioassays indicated that most compounds exhibited promising in vitro antibacterial bioactivities against tobacco bacterial wilt at 200 mu g/mL. The relationship between structure and antibacterial activity was also discussed. Among the title compounds, 5'c:, 5'h, 5'i, and 5, could inhibit mycelia growth of Ralstonia solanacearum in vitro by approximately 50% (EC50) at 39.8, 60.3, 47.9, and 32.1 mu g/mL, respectively. Among them, compound 5) was identified as the most promising candidate due to its stronger effect than that of Kocide 3000 [Cu(OH)(2)] within the same concentration range. Field trials demonstrated that the control effect of compound 55 against tobacco bacterial wilt was better than that of the commercial bactericide Saisentong. For the first time, the present work demonstrated that sulfone derivatives containing 1,3,4-oxadiazole can be used to develop potential bactericides for plants.
• Sulfone-Based Probes Unraveled Dihydrolipoamide <i>S</i>-Succinyltransferase as an Unprecedented Target in Phytopathogens
  作者：Biao Chen、Qingsu Long、Yongliang Zhao、Yuanyuan Wu、Shasha Ge、Peiyi Wang、Cai-Guang Yang、Yonggui Chi、Baoan Song、Song Yang

  DOI：10.1021/acs.jafc.9b02059

  日期：2019.6.26

  Target validation of current drugs remains the major challenge for target-based drug discovery, especially for agrochemical discovery. The bactericide 0 represents a novel lead structure and has shown potent efficacy against those diseases that are extremely difficult to control, such as rice bacterial leaf blight. However, no detailed target analysis of this bactericide has been reported. Here, we developed a panel of 0-derived probes 1-6, in which a conservative modification (alkyne tag) was introduced to keep the antibacterial activity of 0 and provide functionality for target identification via click chemistry. With these cell-permeable probes, we were able to discover dihydrolipoamide S-succinyltransferase (DLST) as an unprecedented target in living cells. The probes showed good preference for DLST, especially probe 1, which demonstrated distinct selectivity and reactivity. Also, we reported 0 as the first covalent DLST inhibitor, which has been used to confirm the involvement of DLST in the regulation of energy production.