(3-oxido-2,1,3-benzoxadiazol-3-ium-5-yl)methyl N'-[(E)-(4-hydroxyphenyl)methylideneamino]carbamimidothioate | 1004980-99-7

• 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: (3-oxido-2,1,3-benzoxadiazol-3-ium-5-yl)methyl N'-[(E)-(4-hydroxyphenyl)methylideneamino]carbamimidothioate
• CAS: 1004980-99-7
• 化学式: C₁₅H₁₃N₅O₃S
• 分子量: 343.366
• InChiKey: HYQHLDOZRBTLBO-CAOOACKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-bromomethyl-benzo[1,2,5]oxadiazole-1-oxide 、 (E)-2-(4-hydroxybenzylidene)hydrazine-1-carbothioamide 在 18-冠醚-6 、 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以27%的产率得到(3-oxido-2,1,3-benzoxadiazol-3-ium-5-yl)methyl N'-[(E)-(4-hydroxyphenyl)methylideneamino]carbamimidothioate
  参考文献：
  名称：

  New trypanocidal hybrid compounds from the association of hydrazone moieties and benzofuroxan heterocycle

  摘要：

  Hybrid compounds containing hydrazones and benzofuroxan pharmacophores were designed as potential Trypanosoma cruzi-enzyme inhibitors. The majority of the designed compounds was successfully synthesized and biologically evaluated displaying remarkable in vitro activity against different strains of T. cruzi. Unspecific cytotoxicity was evaluated using mouse macrophages, displaying isothiosemicarbazone 10 and thiosemicarbazone 12 selectivity indexes (macrophage/parasite) of 21 and 27, respectively. In addition, the mode of anti-trypanosomal action of the derivatives was investigated. Some of these derivatives were moderate inhibitors of cysteinyl active site enzymes of T. cruzi, cruzipain and trypanothione reductase. ESR experiments using T. cruzi microsomal fraction suggest that the main mechanism of action of the trypanocidal effects is the production of oxidative stress into the parasite. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.038

文献信息

• New trypanocidal hybrid compounds from the association of hydrazone moieties and benzofuroxan heterocycle
  作者：Williams Porcal、Paola Hernández、Lucía Boiani、Mariana Boiani、Ana Ferreira、Agustina Chidichimo、Juan J. Cazzulo、Claudio Olea-Azar、Mercedes González、Hugo Cerecetto

  DOI：10.1016/j.bmc.2008.05.038

  日期：2008.7

  Hybrid compounds containing hydrazones and benzofuroxan pharmacophores were designed as potential Trypanosoma cruzi-enzyme inhibitors. The majority of the designed compounds was successfully synthesized and biologically evaluated displaying remarkable in vitro activity against different strains of T. cruzi. Unspecific cytotoxicity was evaluated using mouse macrophages, displaying isothiosemicarbazone 10 and thiosemicarbazone 12 selectivity indexes (macrophage/parasite) of 21 and 27, respectively. In addition, the mode of anti-trypanosomal action of the derivatives was investigated. Some of these derivatives were moderate inhibitors of cysteinyl active site enzymes of T. cruzi, cruzipain and trypanothione reductase. ESR experiments using T. cruzi microsomal fraction suggest that the main mechanism of action of the trypanocidal effects is the production of oxidative stress into the parasite. (c) 2008 Elsevier Ltd. All rights reserved.