5-(2-hydroxyethylthiomethyl)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-(2-hydroxyethylthiomethyl)benzo[1,2-c]-1,2,5-oxadiazole N¹-oxide
• 英文别名: 2-[(1-Oxido-2,1,3-benzoxadiazol-1-ium-5-yl)methylsulfanyl]ethanol
• 化学式: C₉H₁₀N₂O₃S
• 分子量: 226.256
• InChiKey: AOGQELMJPQSCHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(2-hydroxyethylthiomethyl)benzo[1,2-c]-1,2,5-oxadiazole N¹-oxide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到5-(2-hydroxyethylsulfonylmethyl)benzo[1,2-c]-1,2,5-oxadiazole N¹-oxide
  参考文献：
  名称：

  In Vivo Anti-Chagas Vinylthio-, Vinylsulfinyl-, and Vinylsulfonylbenzofuroxan Derivatives

  摘要：

  New benzofuroxans were developed and studied as antiproliferative Trypanosoma cruzi agents. Compounds displayed remarkable in vitro activities against different strains, Tulahuen 2, CL Brener and Y. Its unspecific cytotoxicity was evaluated using human macrophages being not toxic at a concentration at least 8 times, and until 250 times, that of its T. cruzi IC50. Some biochemical pathways were studied, namely parasite respiration, cysteinyl active site enzymes and reaction with glutathione, as target for the mechanism of action. Not only T cruzi respiration but also Cruzipain or trypanothione reductase were not affected, however the most active derivatives, the vinylsulfinyl- and vinylsulfonyl-containing benzofuroxans, react with glutathione in a redox pathway. Furthermore, the compounds showed good in vivo activities when they were studied in an acute murine model of Chagas' disease. The compounds were able to reduce the parasite loads of animals with fully established T cruzi infections.

  DOI：

  10.1021/jm070604e
• 作为产物：
  描述：

  5-(bromomethyl)benzofuroxan 、 2-巯基乙醇 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以40%的产率得到5-(2-hydroxyethylthiomethyl)benzo[1,2-c]-1,2,5-oxadiazole N¹-oxide
  参考文献：
  名称：

  In Vivo Anti-Chagas Vinylthio-, Vinylsulfinyl-, and Vinylsulfonylbenzofuroxan Derivatives

  摘要：

  New benzofuroxans were developed and studied as antiproliferative Trypanosoma cruzi agents. Compounds displayed remarkable in vitro activities against different strains, Tulahuen 2, CL Brener and Y. Its unspecific cytotoxicity was evaluated using human macrophages being not toxic at a concentration at least 8 times, and until 250 times, that of its T. cruzi IC50. Some biochemical pathways were studied, namely parasite respiration, cysteinyl active site enzymes and reaction with glutathione, as target for the mechanism of action. Not only T cruzi respiration but also Cruzipain or trypanothione reductase were not affected, however the most active derivatives, the vinylsulfinyl- and vinylsulfonyl-containing benzofuroxans, react with glutathione in a redox pathway. Furthermore, the compounds showed good in vivo activities when they were studied in an acute murine model of Chagas' disease. The compounds were able to reduce the parasite loads of animals with fully established T cruzi infections.

  DOI：

  10.1021/jm070604e

文献信息

• <i>In Vivo</i> Anti-Chagas Vinylthio-, Vinylsulfinyl-, and Vinylsulfonylbenzofuroxan Derivatives
  作者：Williams Porcal、Paola Hernández、Mariana Boiani、Gabriela Aguirre、Lucía Boiani、Agustina Chidichimo、Juan J. Cazzulo、Nuria E. Campillo、Juan A. Paez、Ana Castro、R. Luise Krauth-Siegel、Carolina Davies、Miguel Ángel Basombrío、Mercedes González、Hugo Cerecetto

  DOI：10.1021/jm070604e

  日期：2007.11.1

  New benzofuroxans were developed and studied as antiproliferative Trypanosoma cruzi agents. Compounds displayed remarkable in vitro activities against different strains, Tulahuen 2, CL Brener and Y. Its unspecific cytotoxicity was evaluated using human macrophages being not toxic at a concentration at least 8 times, and until 250 times, that of its T. cruzi IC50. Some biochemical pathways were studied, namely parasite respiration, cysteinyl active site enzymes and reaction with glutathione, as target for the mechanism of action. Not only T cruzi respiration but also Cruzipain or trypanothione reductase were not affected, however the most active derivatives, the vinylsulfinyl- and vinylsulfonyl-containing benzofuroxans, react with glutathione in a redox pathway. Furthermore, the compounds showed good in vivo activities when they were studied in an acute murine model of Chagas' disease. The compounds were able to reduce the parasite loads of animals with fully established T cruzi infections.