2-amino-5-(2-phenylethenyl)-1,3,4-oxadiazole | 60135-70-8

• 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-amino-5-(2-phenylethenyl)-1,3,4-oxadiazole
• 英文别名: 5-styryl-[1,3,4]oxadiazol-2-ylamine；2-Amino-5-(2-phenyl-vinyl)-<1,3,4>oxadiazol；2-Amino-5-styryl-1,3,4-oxdiazol；5-(2-Phenylethenyl)-1,3,4-oxadiazol-2-amine
• CAS: 60135-70-8
• 化学式: C₁₀H₉N₃O
• 分子量: 187.201
• InChiKey: IVPQAOFOTKZPSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  376.2±35.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-5-(2-phenylethenyl)-1,3,4-oxadiazole 在 ammonium acetate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Expeditious Synthesis, Antimicrobial and Antimalarial Activities of Novel Heterocycles Bearing Imidazole-oxadiazole Based Hybrid Pharmacophores

  摘要：

  A facile synthesis of 2-substituted-5-amino-oxadiazole derivatives has been achieved by refluxing/sonicating a mixture of semicarbazide with various aromatic acids in conc. sulphuric acid alone. The isolated products were further condensed with p-dimethylaminobenzaldehyde/p-hydroxybenzaldehyde to obtain respective imino derivatives. Finally, some potentially biologically active imidazole analogues were obtained by reacting ammonium acetate and 5-bromoisatin with the synthesized imino products. All the newly synthesized compounds were thoroughly characterized by standard analytical techniques. These imidazole-oxadiazole hybrid compounds were also evaluated for their antimicrobial and antimalarial activities. The compounds all exhibited moderate to significant antimicrobial activity (6-10mm, zone of inhibition) and promising antimalarial activity (IC50 0.037-0.100 mu M). This report entails a detailed synthetic procedure, spectroscopic elucidation and activities of the synthesized compounds. Supporting Information for this article is available online at http://www.thieme-connect.de/products

  DOI：

  10.1055/s-0042-112028
• 作为产物：
  描述：

  cinnamaldehyde semicarbazone 在 碘 、 sodium carbonate 、 potassium iodide 作用下， 生成 2-amino-5-(2-phenylethenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Gehlen,H.; Moeckel,K., Justus Liebigs Annalen der Chemie, 1962, vol. 651, p. 133 - 136

  摘要：

  DOI：

文献信息

• Gehlen,H.; Moeckel,K., Justus Liebigs Annalen der Chemie, 1962, vol. 651, p. 133 - 136
  作者：Gehlen,H.、Moeckel,K.

  DOI：——

  日期：——
• Pandey; Ram; Mishra, Journal of the Indian Chemical Society, 1976, vol. 53, # 5, p. 520 - 522
  作者：Pandey、Ram、Mishra

  DOI：——

  日期：——
• Singh, Sushma; Kumar, Sanjeev; Sharma, Laxmi Kant, Journal of the Indian Chemical Society, 2009, vol. 86, # 7, p. 734 - 738
  作者：Singh, Sushma、Kumar, Sanjeev、Sharma, Laxmi Kant、Singh

  DOI：——

  日期：——
• Expeditious Synthesis, Antimicrobial and Antimalarial Activities of Novel Heterocycles Bearing Imidazole-oxadiazole Based Hybrid Pharmacophores
  作者：K. Balaji、P. Bhatt、A. Jha

  DOI：10.1055/s-0042-112028

  日期：——

  A facile synthesis of 2-substituted-5-amino-oxadiazole derivatives has been achieved by refluxing/sonicating a mixture of semicarbazide with various aromatic acids in conc. sulphuric acid alone. The isolated products were further condensed with p-dimethylaminobenzaldehyde/p-hydroxybenzaldehyde to obtain respective imino derivatives. Finally, some potentially biologically active imidazole analogues were obtained by reacting ammonium acetate and 5-bromoisatin with the synthesized imino products. All the newly synthesized compounds were thoroughly characterized by standard analytical techniques. These imidazole-oxadiazole hybrid compounds were also evaluated for their antimicrobial and antimalarial activities. The compounds all exhibited moderate to significant antimicrobial activity (6-10mm, zone of inhibition) and promising antimalarial activity (IC50 0.037-0.100 mu M). This report entails a detailed synthetic procedure, spectroscopic elucidation and activities of the synthesized compounds. Supporting Information for this article is available online at http://www.thieme-connect.de/products