(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methyl-1-[(3-piperidin-1-ylphenyl)sulfonyl]piperazine | 1041389-56-3

• 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-piperidin-1-ylphenyl)sulfonyl]piperazine
• 英文别名: (2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methyl-1-(3-piperidin-1-ylphenyl)sulfonylpiperazine
• CAS: 1041389-56-3
• 化学式: C₂₃H₂₇F₄N₃O₂S
• 分子量: 485.546
• InChiKey: BNJKKTXCOINHEU-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  52.2
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  哌啶 、 (2R)-1-[(3-bromophenyl)sulfonyl]-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazine 在 tris-(dibenzylideneacetone)dipalladium(0) 、 2,2'-bis(di-tert-butylphosphino)biphenyl 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以67%的产率得到(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methyl-1-[(3-piperidin-1-ylphenyl)sulfonyl]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

文献信息

• Piperazine Sulfonamides as Potent, Selective, and Orally Available 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors with Efficacy in the Rat Cortisone-Induced Hyperinsulinemia Model
  作者：Jason Xiang、Zhao-Kui Wan、Huan-Qiu Li、Manus Ipek、Eva Binnun、Jill Nunez、Lihren Chen、John C. McKew、Tarek S. Mansour、Xin Xu、Vipin Suri、May Tam、Yuzhe Xing、Xiangping Li、Seung Hahm、James Tobin、Eddine Saiah

  DOI：10.1021/jm8004948

  日期：2008.7.1

  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.