(4-nitrophenyl)-(4aRS,8aSR)-octahydroisoquinolin-2-ylmethanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (4-nitrophenyl)-(4aRS,8aSR)-octahydroisoquinolin-2-ylmethanone
• 英文别名: [(4aS,8aR)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl]-(4-nitrophenyl)methanone
• 化学式: C₁₆H₂₀N₂O₃
• 分子量: 288.346
• InChiKey: CDEUIZXPPIBTLT-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-nitrophenyl)-(4aRS,8aSR)-octahydroisoquinolin-2-ylmethanone 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以96%的产率得到(4-aminophenyl)-(4aRS,8aSR)-octahydroisoquinolin-2-ylmethanone
  参考文献：
  名称：

  Perhydroquinolylbenzamides as Novel Inhibitors of 11β-Hydroxysteroid Dehydrogenase Type 1

  摘要：

  High-throughput screening identified 5 as a weak inhibitor of 11 beta-HSD1. Optimization of the structure led to a series of perhydroquinolylbenzamides, some with low nanomolar inhibitory potency. A tertiary benzamide is required for biological activity and substitution of the terminal benzamide with either electron-donating or -withdrawing groups is tolerated. The majority of the compounds show selectivity of > 20 to > 700-fold over 11 beta-HSD2. Analogues which showed >50% inhibition of 11 beta-HSD1 at 1 mu M in an cellular assay were screened in an ADX mouse model. A maximal response of > 70% reduction of liver corticosterone levels was observed for three compounds; 9m, 25 and 49.

  DOI：

  10.1021/jm058228q
• 作为产物：
  描述：

  4-硝基苯甲酰氯 、 trans-decahydroisoquinoline 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以66%的产率得到(4-nitrophenyl)-(4aRS,8aSR)-octahydroisoquinolin-2-ylmethanone
  参考文献：
  名称：

  Perhydroquinolylbenzamides as Novel Inhibitors of 11β-Hydroxysteroid Dehydrogenase Type 1

  摘要：

  High-throughput screening identified 5 as a weak inhibitor of 11 beta-HSD1. Optimization of the structure led to a series of perhydroquinolylbenzamides, some with low nanomolar inhibitory potency. A tertiary benzamide is required for biological activity and substitution of the terminal benzamide with either electron-donating or -withdrawing groups is tolerated. The majority of the compounds show selectivity of > 20 to > 700-fold over 11 beta-HSD2. Analogues which showed >50% inhibition of 11 beta-HSD1 at 1 mu M in an cellular assay were screened in an ADX mouse model. A maximal response of > 70% reduction of liver corticosterone levels was observed for three compounds; 9m, 25 and 49.

  DOI：

  10.1021/jm058228q