5-(chloromethyl)benzo<1,2-c>1,2,5-oxadiazole N₁-oxide | 229321-96-4

• 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-(chloromethyl)benzo<1,2-c>1,2,5-oxadiazole N₁-oxide
• 英文别名: 5-chloromethylbenzo[1,2,5]oxadiazole 1-oxide；5-(Chloromethyl)-1-oxido-2,1,3-benzoxadiazol-1-ium
• CAS: 229321-96-4
• 化学式: C₇H₅ClN₂O₂
• 分子量: 184.582
• InChiKey: NYXIOQMGPSMHFS-UHFFFAOYSA-N

物化性质

• 沸点：
  324.5±34.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(chloromethyl)benzo<1,2-c>1,2,5-oxadiazole N₁-oxide 在 18-冠醚-6 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以30%的产率得到5-iodomethylbenzo[1,2,5]oxadiazole 1-oxide
  参考文献：
  名称：

  Benzo[1,2-c]1,2,5-oxadiazole N-oxide derivatives as potential antitrypanosomal drugs. Part 3: Substituents-clustering methodology in the search for new active compounds

  摘要：

  The results of a study on the use of Hansch's series design, cluster methodology, for the generation of newbenzo[1,2-c] 1,2, 5-oxadiazole N-oxide derivatives as antitrypanosomal compounds are described. In vitro activity of these compounds was tested against Tulahuen 2 strain of Trypanosoma cruzi. Clearly, the Hansch methodology allowed identifying two cluster-substituents suitable for further structural modifications. The most effective drugs, derivatives 11, 18, and 21, with 50% inhibitory concentration (IC50) of the same order as that of the reference drug, represent an excellent structural point of chemical modifications for the design of future drugs. Preliminary results from the study of the mechanism of action of these benzofuroxans point to perturbation of the mitochondrial electron chain, inhibiting parasite respiration. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.020
• 作为产物：
  描述：

  6-formylbenzofuroxan 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 生成 6-(chloromethyl)benzo<1,2-c>1,2,5-oxadiazole N₁-oxide 、 5-(chloromethyl)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.
• Benzo[1,2-c]1,2,5-oxadiazole N-oxide derivatives as potential antitrypanosomal drugs. Part 3: Substituents-clustering methodology in the search for new active compounds
  作者：Gabriela Aguirre、Lucía Boiani、Hugo Cerecetto、Rossanna Di Maio、Mercedes González、Williams Porcal、Ana Denicola、Matías Möller、Leonor Thomson、Verónica Tórtora

  DOI：10.1016/j.bmc.2005.05.020

  日期：2005.12

  The results of a study on the use of Hansch's series design, cluster methodology, for the generation of newbenzo[1,2-c] 1,2, 5-oxadiazole N-oxide derivatives as antitrypanosomal compounds are described. In vitro activity of these compounds was tested against Tulahuen 2 strain of Trypanosoma cruzi. Clearly, the Hansch methodology allowed identifying two cluster-substituents suitable for further structural modifications. The most effective drugs, derivatives 11, 18, and 21, with 50% inhibitory concentration (IC50) of the same order as that of the reference drug, represent an excellent structural point of chemical modifications for the design of future drugs. Preliminary results from the study of the mechanism of action of these benzofuroxans point to perturbation of the mitochondrial electron chain, inhibiting parasite respiration. (c) 2005 Elsevier Ltd. All rights reserved.