5-<3-(diethylamino)propylcarbamoyl>benzo<1,2-c>1,2,5-oxadiazole N₁-oxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 5-<3-(diethylamino)propylcarbamoyl>benzo<1,2-c>1,2,5-oxadiazole N₁-oxide
• 英文别名: N-[3-(diethylamino)propyl]-1-oxido-2,1,3-benzoxadiazol-1-ium-5-carboxamide
• 化学式: C₁₄H₂₀N₄O₃
• 分子量: 292.338
• InChiKey: BBQODQNEBBACMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-carboxybenzo[c][1,2,5]oxadiazole 1-oxide 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 5-<3-(diethylamino)propylcarbamoyl>benzo<1,2-c>1,2,5-oxadiazole N₁-oxide
  参考文献：
  名称：

  1,2,5-Oxadiazole N-Oxide Derivatives and Related Compounds as Potential Antitrypanosomal Drugs:  Structure−Activity Relationships

  摘要：

  The syntheses of a new series of derivatives of 1,2,5-oxadiazole N-oxide, benzo[1,2-c]1,2,5-oxadiazole N-oxide, and quinoxaline di-hr-oxide are described. In vitro antitrypanosomal activity of these compounds was tested against epimastigote forms of Trypanosoma cruzi. For the most effective drugs, derivatives IIIe and IIIf, the 50% inhibitory dose (ID50) was determined as well as their cytotoxicity against mammalian fibroblasts. Electrochemical studies and ESR spectroscopy show that the highest activities observed are associated with the facile mono-electronation of the N-oxide moiety. Lipophilic-hydrophilic balance of the compounds could also play an important role in their effectiveness as antichagasic drugs.

  DOI：

  10.1021/jm9805790

文献信息

• 1,2,5-Oxadiazole <i>N</i>-Oxide Derivatives and Related Compounds as Potential Antitrypanosomal Drugs:  Structure−Activity Relationships
  作者：Hugo Cerecetto、Rossanna Di Maio、Mercedes González、Mariela Risso、Patricia Saenz、Gustavo Seoane、Ana Denicola、Gonzalo Peluffo、Celia Quijano、Claudio Olea-Azar

  DOI：10.1021/jm9805790

  日期：1999.6.1

  The syntheses of a new series of derivatives of 1,2,5-oxadiazole N-oxide, benzo[1,2-c]1,2,5-oxadiazole N-oxide, and quinoxaline di-hr-oxide are described. In vitro antitrypanosomal activity of these compounds was tested against epimastigote forms of Trypanosoma cruzi. For the most effective drugs, derivatives IIIe and IIIf, the 50% inhibitory dose (ID50) was determined as well as their cytotoxicity against mammalian fibroblasts. Electrochemical studies and ESR spectroscopy show that the highest activities observed are associated with the facile mono-electronation of the N-oxide moiety. Lipophilic-hydrophilic balance of the compounds could also play an important role in their effectiveness as antichagasic drugs.