β-{[2-(N-acetylamino)-5-methoxycarbonyl-3-nitro]-phenyl}-O-nitro ethanol | 850544-00-2

• 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: β-{[2-(N-acetylamino)-5-methoxycarbonyl-3-nitro]-phenyl}-O-nitro ethanol
• 英文别名: methyl 4-acetamido-3-nitro-5-(2-nitrooxyethyl)benzoate
• CAS: 850544-00-2
• 化学式: C₁₂H₁₃N₃O₈
• 分子量: 327.251
• InChiKey: GIXXMUIDFVIGPE-UHFFFAOYSA-N

物化性质

• 熔点：
  147-150 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  576.1±50.0 °C(Predicted)
• 密度：
  1.459±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  150.91
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  β-{[2-(N-acetylamino)-5-methoxycarbonyl-3-nitro]-phenyl}-O-nitro ethanol 在 platinum(IV) oxide 氢气 、 三乙胺 、 三氟乙酸 、 mercury dichloride 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、206.84 kPa 条件下， 反应 42.75h， 生成 β-{2-amino-3-[amino(imino)methyl]amino-5-carboxyphenyl}ethanol hydrochloride
  参考文献：
  名称：

  Synthesis and inhibitory activity of benzoic acid and pyridine derivatives on influenza neuraminidase

  摘要：

  Based upon the activity and X-ray crystallographic studies of tri-substituted benzene derivatives containing carboxylic acid, acetamido and guanidine groups, we investigated the effect of the fourth substituent to fulfill the fourth pocket of neuraminidase enzyme. The groups selected as fourth substituents were hydroxymethyl, hydroxyethyl, oxime and amino. These tetra-substituted benzene derivatives were synthesized and evaluated for neuraminidase inhibitory activity. All these compounds were found to have poorer IC50 values than the tri-substituted compounds. Further, benzene ring was replaced by pyridine ring and di, tri and tetra-substituted pyridine derivatives were synthesized. The activity of the pyridine derivatives was comparable to benzene derivatives. The fourth substituent seems to disturb the binding of the other three substituents, so the activity is reduced as compared to trisubstituted benzene and pyridine derivatives. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.042
• 作为产物：
  描述：

  β-(2-N-acetylamino-5-methoxycarbonylphenyl)ethanol 在 硝酸 作用下， 反应 1.5h， 以64%的产率得到β-{[2-(N-acetylamino)-5-methoxycarbonyl-3-nitro]-phenyl}-O-nitro ethanol
  参考文献：
  名称：

  Synthesis and inhibitory activity of benzoic acid and pyridine derivatives on influenza neuraminidase

  摘要：

  Based upon the activity and X-ray crystallographic studies of tri-substituted benzene derivatives containing carboxylic acid, acetamido and guanidine groups, we investigated the effect of the fourth substituent to fulfill the fourth pocket of neuraminidase enzyme. The groups selected as fourth substituents were hydroxymethyl, hydroxyethyl, oxime and amino. These tetra-substituted benzene derivatives were synthesized and evaluated for neuraminidase inhibitory activity. All these compounds were found to have poorer IC50 values than the tri-substituted compounds. Further, benzene ring was replaced by pyridine ring and di, tri and tetra-substituted pyridine derivatives were synthesized. The activity of the pyridine derivatives was comparable to benzene derivatives. The fourth substituent seems to disturb the binding of the other three substituents, so the activity is reduced as compared to trisubstituted benzene and pyridine derivatives. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.042