3-nitro-4-nitrooxymethyl-benzaldehyde

• 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: 3-nitro-4-nitrooxymethyl-benzaldehyde
• 英文别名: (4-Formyl-2-nitrophenyl)methyl nitrate
• 化学式: C₈H₆N₂O₆
• 分子量: 226.145
• InChiKey: WZXXSYFCYKRIIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-溴甲基苯甲醛 在 硫酸 、 silver nitrate 、 potassium nitrate 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 26.0h， 生成 3-nitro-4-nitrooxymethyl-benzaldehyde
  参考文献：
  名称：

  NO donors, part 8 []: synthesis and vasodilating activities of substituted benzylnitrates compared to cyclohexylmethylnitrate and GTN

  摘要：

  A series of substituted benzylnitrates (1) and the formally but not chemically similar cyclohexylmethylnitrate (CHMN) have been synthesised. Vasodilating activities were measured on endothelium-intact and N-G-nitro-(L)-arginine ((L)-NNA)-blocked porcine right coronary arteries, precontracted with prostaglandin F-2alpha (PGF(2alpha)). Glyceroltrinitrate (GTN) was used as reference. In intact coronary arteries the vasodilating activities of all benzylnitrates are lower compared with GTN, but higher compared with CHMN. However, blocking the function of the endothelium by L-NNA, the activity of all benzy1nitrates increased, whereas that of CHMN and GTN remained nearly unaffected. Under these conditions, the mononitrates 4-nitro-benzylnitrate (1c) and 4-nitrooxymethyl-benzonitrile (1h) even showed higher vasodilator activities than the trinitrate GTN and in general, vasorelaxation by the benzy1nitrates as defined by the concentrations for half maximal effects (EC50 values) was found to be 2-3 orders of magnitude higher than that induced by CHMN. The study demonstrates that the in vitro activities of organic nitrates do not correlate with the number of nitrate groups within the molecule nor to the lipophilicity of the molecules. Instead, vasodilator activity is highly sensitive to the structure and the type of the substituents in the molecular carrier of the nitrate group. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00079-5

文献信息

• NO donors, part 8 []: synthesis and vasodilating activities of substituted benzylnitrates compared to cyclohexylmethylnitrate and GTN
  作者：C Weßler

  DOI：10.1016/s0223-5234(03)00079-5

  日期：2003.6

  A series of substituted benzylnitrates (1) and the formally but not chemically similar cyclohexylmethylnitrate (CHMN) have been synthesised. Vasodilating activities were measured on endothelium-intact and N-G-nitro-(L)-arginine ((L)-NNA)-blocked porcine right coronary arteries, precontracted with prostaglandin F-2alpha (PGF(2alpha)). Glyceroltrinitrate (GTN) was used as reference. In intact coronary arteries the vasodilating activities of all benzylnitrates are lower compared with GTN, but higher compared with CHMN. However, blocking the function of the endothelium by L-NNA, the activity of all benzy1nitrates increased, whereas that of CHMN and GTN remained nearly unaffected. Under these conditions, the mononitrates 4-nitro-benzylnitrate (1c) and 4-nitrooxymethyl-benzonitrile (1h) even showed higher vasodilator activities than the trinitrate GTN and in general, vasorelaxation by the benzy1nitrates as defined by the concentrations for half maximal effects (EC50 values) was found to be 2-3 orders of magnitude higher than that induced by CHMN. The study demonstrates that the in vitro activities of organic nitrates do not correlate with the number of nitrate groups within the molecule nor to the lipophilicity of the molecules. Instead, vasodilator activity is highly sensitive to the structure and the type of the substituents in the molecular carrier of the nitrate group. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.