methyl 2-[3-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)phenoxy]-2-methylpropanoate | 1041389-63-2

• 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: methyl 2-[3-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)phenoxy]-2-methylpropanoate
• CAS: 1041389-63-2
• 化学式: C₂₃H₂₆F₄N₂O₅S
• 分子量: 518.529
• InChiKey: UKILOEHMVCTRRL-OAHLLOKOSA-N

物化性质

• 沸点：
  582.3±60.0 °C(predicted)
• 密度：
  1.325±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  76.15
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2-[3-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)phenoxy]-2-methylpropanoate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以65.6%的产率得到2-[3-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)phenoxy]-2-methylpropanoic acid
  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：

  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