3-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)phenol | 946397-52-0

• 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: 3-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)phenol
• 英文别名: 3-[(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl]sulfonylphenol
• CAS: 946397-52-0
• 化学式: C₁₈H₁₈F₄N₂O₃S
• 分子量: 418.412
• InChiKey: IOCYUFPCUUUCIH-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.2
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-溴代异丁酸甲酯 、 3-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)phenol 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.83h， 以88%的产率得到methyl 2-[3-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)phenoxy]-2-methylpropanoate
  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：

  (2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-1-(3-methoxyphenylsulfonyl)-2-methylpiperazine 在 三溴化硼 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.0h， 以96%的产率得到3-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)phenol
  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

文献信息

• 11-Beta HSD 1 inhibitors
  申请人：Xiang Shaoyun Jason

  公开号：US20070219198A1

  公开（公告）日：2007-09-20

  This invention relates to inhibiting 11βHSD1.

  该发明涉及抑制11βHSD1。
• 11-Beta HSD1 Inhibitors
  申请人：Xiang Jason Shaoyun

  公开号：US20100029648A1

  公开（公告）日：2010-02-04

  This invention relates to inhibiting 11βHSD1.

  本发明涉及抑制11βHSD1。
• 11-beta HSD1 inhibitors
  申请人：Wyeth

  公开号：US07632838B2

  公开（公告）日：2009-12-15

  This invention relates to inhibiting 11βHSD1.

  本发明涉及抑制11βHSD1的方法。
• US7632838B2
  申请人：——

  公开号：US7632838B2

  公开（公告）日：2009-12-15