(E)-3-methyl-4-((2-(4-nitrobenzoyl)hydrazono)methyl)-1,2,5-oxadiazole 2-oxide | 1617522-09-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3-methyl-4-((2-(4-nitrobenzoyl)hydrazono)methyl)-1,2,5-oxadiazole 2-oxide
• 英文别名: N-[(E)-(4-methyl-5-oxido-1,2,5-oxadiazol-5-ium-3-yl)methylideneamino]-4-nitrobenzamide
• CAS: 1617522-09-4
• 化学式: C₁₁H₉N₅O₅
• 分子量: 291.223
• InChiKey: IWNNJNPYZHDHJJ-WUXMJOGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  对硝基苯甲酸 在 盐酸 、 硫酸 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 (E)-3-methyl-4-((2-(4-nitrobenzoyl)hydrazono)methyl)-1,2,5-oxadiazole 2-oxide 、 (Z)-3-methyl-4-((2-(4-nitrobenzoyl)hydrazono)methyl)-1,2,5-oxadiazole 2-oxide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of hybrid bioisoster derivatives of N-acylhydrazone and furoxan groups with potential and selective anti-Trypanosoma cruzi activity

  摘要：

  Hybrid bioisoster derivatives from N-acylhydrazones and furoxan groups were designed with the objective of obtaining at least a dual mechanism of action: cruzain inhibition and nitric oxide (NO) releasing activity. Fifteen designed compounds were synthesized varying the substitution in N-acylhydrazone and in furoxan group as well. They had its anti-Trypanosoma cruzi activity in amastigotes forms, NO releasing potential and inhibitory cruzain activity evaluated. The two most active compounds (6,14) both in the parasite amastigotes and in the enzyme contain the nitro group in para position of the aromatic ring. The permeability screening in Caco-2 cell and cytotoxicity assay in human cells were performed for those most active compounds and both showed to be less cytotoxic than the reference drug, benznidazole. Compound 6 was the most promising, since besides activity it showed good permeability and selectivity index, higher than the reference drug. Thereby the compound 6 was considered as a possible candidate for additional studies. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.077

文献信息

• Design, synthesis and biological evaluation of hybrid bioisoster derivatives of N-acylhydrazone and furoxan groups with potential and selective anti-Trypanosoma cruzi activity
  作者：Ricardo Augusto Massarico Serafim、José Eduardo Gonçalves、Felipe Pereira de Souza、Ana Paula de Melo Loureiro、Silvia Storpirtis、Renata Krogh、Adriano Defini Andricopulo、Luiz Carlos Dias、Elizabeth Igne Ferreira

  DOI：10.1016/j.ejmech.2014.05.077

  日期：2014.7

  Hybrid bioisoster derivatives from N-acylhydrazones and furoxan groups were designed with the objective of obtaining at least a dual mechanism of action: cruzain inhibition and nitric oxide (NO) releasing activity. Fifteen designed compounds were synthesized varying the substitution in N-acylhydrazone and in furoxan group as well. They had its anti-Trypanosoma cruzi activity in amastigotes forms, NO releasing potential and inhibitory cruzain activity evaluated. The two most active compounds (6,14) both in the parasite amastigotes and in the enzyme contain the nitro group in para position of the aromatic ring. The permeability screening in Caco-2 cell and cytotoxicity assay in human cells were performed for those most active compounds and both showed to be less cytotoxic than the reference drug, benznidazole. Compound 6 was the most promising, since besides activity it showed good permeability and selectivity index, higher than the reference drug. Thereby the compound 6 was considered as a possible candidate for additional studies. (C) 2014 Elsevier Masson SAS. All rights reserved.