6-(Butylcarbamoyl)Benzo[C][1,2,5]Oxadiazole1-Oxide | 229322-29-6

• 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: 6-(Butylcarbamoyl)Benzo[C][1,2,5]Oxadiazole1-Oxide
• 英文别名: N-butyl-3-oxido-2,1,3-benzoxadiazol-3-ium-5-carboxamide
• CAS: 229322-29-6
• 化学式: C₁₁H₁₃N₃O₃
• 分子量: 235.243
• InChiKey: KEKGMNQODRGSJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(Butylcarbamoyl)Benzo[C][1,2,5]Oxadiazole1-Oxide 在 劳森试剂 作用下， 反应 0.1h， 以88%的产率得到1-oxy-benzo[1,2,5]oxadiazole-5-carbothionic acid
  参考文献：
  名称：

  Benzo[1, 2-c]1, 2, 5-oxadiazole N-Oxide 衍生物作为潜在的抗锥虫药。结构-活动关系。第二部分

  摘要：

  描述了苯并 [1, 2-c]1, 2, 5-恶二唑 N-氧化物的新衍生物的制备。选择这些衍生物是为了研究和确认先前发现的表现出足够的抗锥虫活性所必需的结构特征。合成的化合物在体外针对克氏锥虫的上鞭毛体形式进行了测试。苯并系统中溴原子的存在产生的化合物活性低于相应的脱卤类似物。然而，5-(溴甲基)-7-溴苯并 [1, 2-c] 恶二唑 N-氧化物 (23) 是对 T. cruzi 最具细胞毒性的化合物。为此，确定了 50% 抑制剂量 (ID50)，它与 ​​Nifurtimox 的数量级相同。

  DOI：

  10.1002/1521-4184(200201)335:1<15::aid-ardp15>3.0.co;2-8
• 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 6-(Butylcarbamoyl)Benzo[C][1,2,5]Oxadiazole1-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

• Synthesis and Herbicidal Activity of <i>N</i>-Oxide Derivatives
  作者：Hugo Cerecetto、Eduardo Dias、Rossanna Di Maio、Mercedes González、Sandra Pacce、Patricia Saenz、Gustavo Seoane、Leopoldo Suescun、Alvaro Mombrú、Grisel Fernández、Marisa Lema、Juana Villalba

  DOI：10.1021/jf9904766

  日期：2000.7.1

  As part of an ongoing program on the chemistry and biological activity of N-oxide-containing molecules, a number of novel 1,2, 5-oxadiazole N-oxide, benzo[1,2-c]1,2,5-oxadiazole N-oxide, and quinoxaline N,N'-dioxide derivatives were synthesized and evaluated for their herbicidal activity. Many of these compounds exhibited moderate to good herbicidal pre-emergence activity against Triticum aestivum

  作为正在进行的有关含氮氧化物分子化学和生物学活性的计划的一部分，许多新型的1,2,5-恶二唑N-氧化物，苯并[1,2-c] 1,2,5-恶二唑合成了N-氧化物和喹喔啉N，N'-二氧化物衍生物，并对其除草活性进行了评估。这些化合物中有许多对普通小麦表现出中等至良好的除草前出苗活性。在更具代表性的化合物（12、20和26）上进行了剂量反应研究。活性最强的丁基氨基甲酰基苯并[1,2-c] 1,2,5-恶二唑N-氧化物26在低至24 g / ha的浓度下表现出除草活性。
• 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.
• Benzo[1, 2-c]1, 2, 5-oxadiazole N-Oxide Derivatives as Potential Antitrypanosomal Drugs. Structure-Activity Relationships. Part II
  作者：Gabriela Aguirre、Hugo Cerecetto、Rossanna Di Maio、Mercedes González、Williams Porcal、Gustavo Seoane、Miguel A. Ortega、Ignacio Aldana、Antonio Monge、Ana Denicola

  DOI：10.1002/1521-4184(200201)335:1<15::aid-ardp15>3.0.co;2-8

  日期：2002.1

  The preparation of new derivatives of benzo[1, 2‐c]1, 2, 5‐oxadiazole N‐oxide is described. These derivatives were chosen in order to investigate and confirmprevious structural features found necessary to display an adequate antitrypanosomal activity. The compounds synthesized were tested in vitro against epimastigote forms of Trypanosoma cruzi.The presence of a bromine atom in the benzo system produced

  描述了苯并 [1, 2-c]1, 2, 5-恶二唑 N-氧化物的新衍生物的制备。选择这些衍生物是为了研究和确认先前发现的表现出足够的抗锥虫活性所必需的结构特征。合成的化合物在体外针对克氏锥虫的上鞭毛体形式进行了测试。苯并系统中溴原子的存在产生的化合物活性低于相应的脱卤类似物。然而，5-(溴甲基)-7-溴苯并 [1, 2-c] 恶二唑 N-氧化物 (23) 是对 T. cruzi 最具细胞毒性的化合物。为此，确定了 50% 抑制剂量 (ID50)，它与 ​​Nifurtimox 的数量级相同。