1-Methyl-2,6-bis-(2-nitro-phenyl)-4-oxo-piperidine-3,5-dicarboxylic acid dimethyl ester | 40328-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-Methyl-2,6-bis-(2-nitro-phenyl)-4-oxo-piperidine-3,5-dicarboxylic acid dimethyl ester
• 英文别名: Dimethyl 1-methyl-2,6-bis(2-nitrophenyl)-4-oxopiperidine-3,5-dicarboxylate
• CAS: 40328-48-1
• 化学式: C₂₂H₂₁N₃O₉
• 分子量: 471.423
• InChiKey: JWNTXLILAHLWDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  165
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 1-Methyl-2,6-bis-(2-nitro-phenyl)-4-oxo-piperidine-3,5-dicarboxylic acid dimethyl ester 、 甲胺 以 甲醇 、 水 为溶剂， 生成 (1S,2S,4R,5R)-3,7-Dimethyl-2,4-bis-(2-nitro-phenyl)-9-oxo-3,7-diaza-bicyclo[3.3.1]nonane-1,5-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Synthesis and Opioid Receptor Affinity of a Series of 2,4-Diaryl-Substituted 3,7-Diazabicylononanones

  摘要：

  3,7-Diazabicyclo[3.3.1]nonan-9-ones having aryl rings in positions 2 and 4 with systematically varied substituents were synthesized using a double Mannich procedure. Radioligand binding assays were performed to measure the affinity of the compounds to the mu-, delta-, and kappa-opioid receptors. The affinity of all 2,4-diphenyl-substituted 3,7-diazabicyclo[3.3.1]nonan-9-ones to the mu- and delta-receptors was found to be low. In contrast, with exception of the nitro- and cyanophenyl-substituted compounds, most of the diazabicycles showed considerable affinity for the kappa-receptor. In particular, the m-fluoro-, p-methoxy-, and m-hydroxy-substituted compounds have an affinity in the submicromolar range. Due to solubility problems in aqueous media, salts of HZ2 were synthesized. The methiodide shows high kappa-affinity and may, thus, be a promising candidate for development of a peripheral kappa-agonist, e.g. for use in the case of rheumatoid arthritis.

  DOI：

  10.1021/jm0009484
• 作为产物：
  描述：

  1,3-丙酮二羧酸二甲酯 、 甲胺 、 邻硝基苯甲醛 以 甲醇 、 水 为溶剂， 生成 1-Methyl-2,6-bis-(2-nitro-phenyl)-4-oxo-piperidine-3,5-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Synthesis and Opioid Receptor Affinity of a Series of 2,4-Diaryl-Substituted 3,7-Diazabicylononanones

  摘要：

  3,7-Diazabicyclo[3.3.1]nonan-9-ones having aryl rings in positions 2 and 4 with systematically varied substituents were synthesized using a double Mannich procedure. Radioligand binding assays were performed to measure the affinity of the compounds to the mu-, delta-, and kappa-opioid receptors. The affinity of all 2,4-diphenyl-substituted 3,7-diazabicyclo[3.3.1]nonan-9-ones to the mu- and delta-receptors was found to be low. In contrast, with exception of the nitro- and cyanophenyl-substituted compounds, most of the diazabicycles showed considerable affinity for the kappa-receptor. In particular, the m-fluoro-, p-methoxy-, and m-hydroxy-substituted compounds have an affinity in the submicromolar range. Due to solubility problems in aqueous media, salts of HZ2 were synthesized. The methiodide shows high kappa-affinity and may, thus, be a promising candidate for development of a peripheral kappa-agonist, e.g. for use in the case of rheumatoid arthritis.

  DOI：

  10.1021/jm0009484