2-(4-chloro-3-nitrophenyl)-5-(ethylsulfanyl)-1,3,4-oxadiazole | 1356585-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-chloro-3-nitrophenyl)-5-(ethylsulfanyl)-1,3,4-oxadiazole
• 英文别名: 2-(4-Chloro-3-nitrophenyl)-5-ethylsulfanyl-1,3,4-oxadiazole；2-(4-chloro-3-nitrophenyl)-5-ethylsulfanyl-1,3,4-oxadiazole
• CAS: 1356585-48-2
• 化学式: C₁₀H₈ClN₃O₃S
• 分子量: 285.711
• InChiKey: HBQLRUZQJOQPCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-chloro-3-nitrophenyl)-5-(ethylsulfanyl)-1,3,4-oxadiazole 在 potassium permanganate 、 溶剂黄146 作用下， 反应 0.17h， 生成 2-(4-Chloro-3-nitrophenyl)-5-ethylsulfonyl-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：

  4-氯-3-硝基苯甲酸 在 硫酸 、 一水合肼 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 2-(4-chloro-3-nitrophenyl)-5-(ethylsulfanyl)-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 and<i>In Vitro</i>Antimicrobial Activity of 1,3,4-Oxadiazole-2-thiol and its Analogs
  作者：R. Galge、A. Raju、M. S. Degani、B. N. Thorat

  DOI：10.1002/jhet.2042

  日期：2015.3

  The present communication deals with the synthesis of 1,3,4‐oxadiazole‐2‐thiol derivatives containing cyclic secondary amines such as morpholine, N‐methyl piperizine, and piperizine. The structural elucidation is based on the spectral data (IR, 1H NMR, and 13C NMR) .The newly synthesized compounds were then tested for their antimicrobial activity against a representative panel of micro‐organisms such

  本通报涉及1,3,4-恶二唑-2-硫醇衍生物的合成，该衍生物含有环状仲胺，例如吗啉，N-甲基哌嗪和哌嗪。结构解析基于光谱数据（IR，1 H NMR和13 C NMR），然后测试新合成的化合物对代表性微生物（如枯草芽孢杆菌，大肠杆菌和念珠菌）的抗菌活性白色的分别使用环丙沙星和氟康唑作为细菌和真菌的参考药物。这些合成的化合物对选定的细菌显示出中等至潜在的抗菌和抗真菌活性，范围分别为6–50μM和针对最常见的真菌，其范围为12–50μM。