2-(2-Bromophenyl)-5-methylsulfanyl-1,3,4-oxadiazole

• 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-(2-Bromophenyl)-5-methylsulfanyl-1,3,4-oxadiazole
• 化学式: C₉H₇BrN₂OS
• 分子量: 271.137
• InChiKey: AQNJWAMFGRAQRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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-(2-Bromophenyl)-5-methylsulfanyl-1,3,4-oxadiazole 在 potassium permanganate 、 溶剂黄146 作用下， 反应 0.17h， 生成 2-(2-Bromophenyl)-5-methylsulfonyl-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
• 作为产物：
  描述：

  邻溴苯甲酸甲酯 在 一水合肼 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 2-(2-Bromophenyl)-5-methylsulfanyl-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

• Synthesis of novel 5-aryl-2-thio-1,3,4-oxadiazoles and the study of their structure–anti-mycobacterial activities
  作者：Fliur Macaev、Ghenadie Rusu、Serghei Pogrebnoi、Alexandru Gudima、Eugenia Stingaci、Ludmila Vlad、Nathaly Shvets、Fatma Kandemirli、Anatholy Dimoglo、Robert Reynolds

  DOI：10.1016/j.bmc.2005.05.011

  日期：2005.8

  The preparation of novel 5-aryt-2-thio-1,3,4-oxadiazoles 4a 41 and the computer-aided study of their in vitro anti-tubercular activity against Myeobacterium tuberculosis H(37)Rv (ATCC 27294) are reported. The average accuracy of the electronic-topological method and neural network methods applied to the activity prediction in leave-one-out cross validation is 80%. (c) 2005 Elsevier Ltd. All rights reserved.