2-Chloro-5-(2-nitro-benzylsulfanyl)-[1,3,4]thiadiazole | 868739-29-1

• 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-Chloro-5-(2-nitro-benzylsulfanyl)-[1,3,4]thiadiazole
• 英文别名: 2-Chloro-5-[(2-nitrophenyl)methylsulfanyl]-1,3,4-thiadiazole
• CAS: 868739-29-1
• 化学式: C₉H₆ClN₃O₂S₂
• 分子量: 287.751
• InChiKey: MILIWUQSNFLDKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Chloro-5-(2-nitro-benzylsulfanyl)-[1,3,4]thiadiazole 在 双氧水 、 碳酸氢钠 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-Cyclopropyl-6-fluoro-7-{4-[5-(2-nitro-phenylmethanesulfonyl)-[1,3,4]thiadiazol-2-yl]-piperazin-1-yl}-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and antibacterial activity of N-(5-benzylthio-1,3,4-thiadiazol-2-yl) and N-(5-benzylsulfonyl-1,3,4-thiadiazol-2-yl)piperazinyl quinolone derivatives

  摘要：

  A series of N-(5-benzylthio-1,3,4-thiadiazol-2-yl) and N-(5-benzylsulfonyl-1,3,4-thiadiazol-2-yl) derivatives of piperazinyl quinolones was synthesized and evaluated for antibacterial activity against Gram-positive and Gram-negative microorganisms. Some of these derivatives exhibit high activity against Gram-positive bacteria; Staphylococcus aureus and Staphylococcus epidermidis, comparable or more potent than their parent N-piperazinyl quinolones norfloxacin and ciprofloxacin as reference drugs. The SAR of this series indicates that both the structure of the benzyl unit and the S or SO2 linker dramatically impact antibacterial activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.016
• 作为产物：
  描述：

  5-(2-Nitro-benzylsulfanyl)-[1,3,4]thiadiazol-2-ylamine 在 盐酸 、 铜 、 sodium nitrite 作用下， 反应 3.0h， 生成 2-Chloro-5-(2-nitro-benzylsulfanyl)-[1,3,4]thiadiazole
  参考文献：
  名称：

  Synthesis and antibacterial activity of N-(5-benzylthio-1,3,4-thiadiazol-2-yl) and N-(5-benzylsulfonyl-1,3,4-thiadiazol-2-yl)piperazinyl quinolone derivatives

  摘要：

  A series of N-(5-benzylthio-1,3,4-thiadiazol-2-yl) and N-(5-benzylsulfonyl-1,3,4-thiadiazol-2-yl) derivatives of piperazinyl quinolones was synthesized and evaluated for antibacterial activity against Gram-positive and Gram-negative microorganisms. Some of these derivatives exhibit high activity against Gram-positive bacteria; Staphylococcus aureus and Staphylococcus epidermidis, comparable or more potent than their parent N-piperazinyl quinolones norfloxacin and ciprofloxacin as reference drugs. The SAR of this series indicates that both the structure of the benzyl unit and the S or SO2 linker dramatically impact antibacterial activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.016