(2R)-4-(4-fluoro-2-(trifluoromethyl)phenyl)-2-methyl-1-(3-nitrobenzenesulfonyl)piperazine | 946400-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (2R)-4-(4-fluoro-2-(trifluoromethyl)phenyl)-2-methyl-1-(3-nitrobenzenesulfonyl)piperazine
• CAS: 946400-01-7
• 化学式: C₁₈H₁₇F₄N₃O₄S
• 分子量: 447.41
• InChiKey: AEOVLXCZALNJNV-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.76
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R)-4-(4-fluoro-2-(trifluoromethyl)phenyl)-2-methyl-1-(3-nitrobenzenesulfonyl)piperazine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以62%的产率得到3-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)aniline
  参考文献：
  名称：

  Piperazine Sulfonamides as Potent, Selective, and Orally Available 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors with Efficacy in the Rat Cortisone-Induced Hyperinsulinemia Model

  摘要：

  11 beta-hydroxysteroid dehydrogenase type 1 (11 beta-HSD1) is the enzyme that converts cortisone to cortisol. Evidence suggests that selective inhibition of 11 beta-HSD1 could treat diabetes and metabolic syndrome. Presented herein are the synthesis, structure-activity relationship, and in vivo evaluation of piperazine sulfonamides as 11 beta HSD1 inhibitors. Through modification of our initial lead 5a, we have identified potent and selective 11 beta-HSD1 inhibitors such as 13q and 13u with good pharmacokinetic properties.

  DOI：

  10.1021/jm8004948
• 作为产物：
  描述：

  (3R)-1-(4-氟-2-(三氟甲基)苯基)-3-甲基哌嗪 、 3-硝基苯磺酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到(2R)-4-(4-fluoro-2-(trifluoromethyl)phenyl)-2-methyl-1-(3-nitrobenzenesulfonyl)piperazine
  参考文献：
  名称：

  Piperazine Sulfonamides as Potent, Selective, and Orally Available 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors with Efficacy in the Rat Cortisone-Induced Hyperinsulinemia Model

  摘要：

  11 beta-hydroxysteroid dehydrogenase type 1 (11 beta-HSD1) is the enzyme that converts cortisone to cortisol. Evidence suggests that selective inhibition of 11 beta-HSD1 could treat diabetes and metabolic syndrome. Presented herein are the synthesis, structure-activity relationship, and in vivo evaluation of piperazine sulfonamides as 11 beta HSD1 inhibitors. Through modification of our initial lead 5a, we have identified potent and selective 11 beta-HSD1 inhibitors such as 13q and 13u with good pharmacokinetic properties.

  DOI：

  10.1021/jm8004948