5-N-(4-tolyl)aminomethyl-3H-1,3,4-oxadiazole-2-thione | 162693-64-3

• 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: 5-N-(4-tolyl)aminomethyl-3H-1,3,4-oxadiazole-2-thione
• 英文别名: 5-{[(4-Methylphenyl)amino]methyl}-1,3,4-oxadiazole-2-thiol；5-[(4-methylanilino)methyl]-3H-1,3,4-oxadiazole-2-thione
• CAS: 162693-64-3
• 化学式: C₁₀H₁₁N₃OS
• 分子量: 221.283
• InChiKey: GVTXJRGATYNVHY-UHFFFAOYSA-N

物化性质

• 熔点：
  155-156 °C(Solv: ethanol (64-17-5))
• 沸点：
  349.0±44.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  77.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-N-(4-tolyl)aminomethyl-3H-1,3,4-oxadiazole-2-thione 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以74%的产率得到5-N-(4-tolyl)aminomethyl-2-((oxiran-2-yl)methylsulfanyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and Antiviral Evaluation of Some 5‐N‐Arylaminomethyl‐2‐glycosylsulphanyl‐1,3,4‐oxadiazoles and Their Analogs against Hepatitis A and Herpes Simplex Viruses

  摘要：

  N-Arylaminomethyl-3H-1,3,4-oxadiazole-2-thiones 2a,b were prepared from the corresponding N-arylglycinoylhydrazides. A number of their thioglycoside derivatives 4-7a-c and S-functionalized analogs 8-11a,b were synthesized by the reaction with different acetobromosugars and acyclic hydroxyalkylating agents. The antiviral activity of a number of the synthesized compounds against herpes simplex virus type 1 (HSV-1) and hepatitis A virus (HAV) was evaluated. Compounds 5a and 5b showed promising results against HAV.

  DOI：

  10.1080/07328300802262778
• 作为产物：
  描述：

  二硫化碳 、 对甲苯氨基乙酸肼 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 15.0h， 以81%的产率得到5-N-(4-tolyl)aminomethyl-3H-1,3,4-oxadiazole-2-thione
  参考文献：
  名称：

  Synthesis and Antiviral Evaluation of Some 5‐N‐Arylaminomethyl‐2‐glycosylsulphanyl‐1,3,4‐oxadiazoles and Their Analogs against Hepatitis A and Herpes Simplex Viruses

  摘要：

  N-Arylaminomethyl-3H-1,3,4-oxadiazole-2-thiones 2a,b were prepared from the corresponding N-arylglycinoylhydrazides. A number of their thioglycoside derivatives 4-7a-c and S-functionalized analogs 8-11a,b were synthesized by the reaction with different acetobromosugars and acyclic hydroxyalkylating agents. The antiviral activity of a number of the synthesized compounds against herpes simplex virus type 1 (HSV-1) and hepatitis A virus (HAV) was evaluated. Compounds 5a and 5b showed promising results against HAV.

  DOI：

  10.1080/07328300802262778

文献信息

• Synthesis and Antiviral Evaluation of Novel 5-(N-Aryl-aminomethyl-1,3,4-oxadiazol-2-yl)hydrazines and Their Sugars, 1,2,4-Triazoles, Tetrazoles and Pyrazolyl Derivatives
  作者：Mohammed T. Abdel-Aal、Waled A. El-Sayed、Salah M. El-Kosy、El Sayed H. El-Ashry

  DOI：10.1002/ardp.200700154

  日期：2008.5

  anhydride. A number of the synthesized compounds were tested for their antiviral activity against herpes simplex virus type‐1 (HSV‐1) and hepatitis‐A virus (HAV, MBBcell culture‐adapted strain). The results revealed that the sugar hydrazones 6a,b showed higher antiviral activity compared to the other hydrazones and their acetylated derivatives.

  制备了许多新的 N-芳基氨基甲基-1,3,4-恶二唑衍生物 2、3a、b 和 9-12a、b。糖（5-N-芳基氨基甲基-1,3,4-恶二唑-2-基）腙4-6a、b是通过肼衍生物3a、b与相应的单糖反应合成的。新的无环-C-核苷7、8a、b是通过糖腙4、5a、b与乙酸酐杂环化制备的。测试了许多合成化合物对 1 型单纯疱疹病毒 (HSV-1) 和甲型肝炎病毒 (HAV，MBB 细胞培养适应株) 的抗病毒活性。结果表明，与其他腙及其乙酰化衍生物相比，糖腙6a、b显示出更高的抗病毒活性。