1-[4-[(2S)-2-methylpiperidin-1-yl]sulfonylphenyl]ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[4-[(2S)-2-methylpiperidin-1-yl]sulfonylphenyl]ethanone
• 化学式: C₁₄H₁₉NO₃S
• 分子量: 281.376
• InChiKey: CEJQPJZKUDGSLA-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[4-[(2S)-2-methylpiperidin-1-yl]sulfonylphenyl]ethanone 、 (三氟甲基)三甲基硅烷 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以45%的产率得到2-(S)-2-methyl-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenylsulfonyl)piperidine
  参考文献：
  名称：

  Discovery of Novel, Potent Benzamide Inhibitors of 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD1) Exhibiting Oral Activity in an Enzyme Inhibition ex Vivo Model^▽

  摘要：

  We report the discovery of potent benzamide inhibitors of 11beta-hydroxysteroid dehydrogenase (11beta-HSD1). The optimization and correlation of in vitro and in vivo metabolic stability will be described. Through modifications to our initial lead 2, we discovered pyridyl compound 13. This compound has a favorable pharmacokinetic profile across three species and showed a dose-dependent decrease in adipose 11beta-HSD1 activity in a monkey ex vivo pharmacodynamic model.

  DOI：

  10.1021/jm800310g
• 作为产物：
  描述：

  4-乙酰基苯磺酰氯 、 (S)-(+)-2-甲基哌啶 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以68%的产率得到1-[4-[(2S)-2-methylpiperidin-1-yl]sulfonylphenyl]ethanone
  参考文献：
  名称：

  Discovery of Novel, Potent Benzamide Inhibitors of 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD1) Exhibiting Oral Activity in an Enzyme Inhibition ex Vivo Model^▽

  摘要：

  We report the discovery of potent benzamide inhibitors of 11beta-hydroxysteroid dehydrogenase (11beta-HSD1). The optimization and correlation of in vitro and in vivo metabolic stability will be described. Through modifications to our initial lead 2, we discovered pyridyl compound 13. This compound has a favorable pharmacokinetic profile across three species and showed a dose-dependent decrease in adipose 11beta-HSD1 activity in a monkey ex vivo pharmacodynamic model.

  DOI：

  10.1021/jm800310g