(1R,2S,3S,4R,5S,7S)-2,4-Bis-(2-chloro-phenyl)-3,7-dimethyl-9-oxo-3,7-diaza-bicyclo[3.3.1]nonane-1,5-dicarboxylic acid dimethyl ester | 97577-03-2

• 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: (1R,2S,3S,4R,5S,7S)-2,4-Bis-(2-chloro-phenyl)-3,7-dimethyl-9-oxo-3,7-diaza-bicyclo[3.3.1]nonane-1,5-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl (1S,2R,4S,5R)-2,4-bis(2-chlorophenyl)-3,7-dimethyl-9-oxo-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarboxylate
• CAS: 97577-03-2
• 化学式: C₂₅H₂₆Cl₂N₂O₅
• 分子量: 505.398
• InChiKey: PBLCUJUZEZUWNJ-YQXZIBMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 Dimethyl 2,6-bis(2-chlorophenyl)-1-methyl-4-oxopiperidine-3,5-dicarboxylate 、 甲胺 以 甲醇 、 水 为溶剂， 生成 (1R,2S,3S,4R,5S,7S)-2,4-Bis-(2-chloro-phenyl)-3,7-dimethyl-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

文献信息

• Caujolle, Raymond; Castera, Pierre; Lattes, Armand, Bulletin de la Societe Chimique de France, 1984, vol. 2, # 9-10, p. 413 - 416
  作者：Caujolle, Raymond、Castera, Pierre、Lattes, Armand

  DOI：——

  日期：——
• Synthesis and Opioid Receptor Affinity of a Series of 2,4-Diaryl-Substituted 3,7-Diazabicylononanones
  作者：Tom Siener、Antonella Cambareri、Ulrich Kuhl、Werner Englberger、Michael Haurand、Babette Kögel、Ulrike Holzgrabe

  DOI：10.1021/jm0009484

  日期：2000.10.1

  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.