Methanone,[4-[[3-(1H-1,2,4-triazol-5-yl)-5-(trifluoromethyl)phenyl]sulfonyl]-1-piperazinyl][(1R,2R)-2-[4-(trifluoromethyl)phenyl]cyclopropyl]- | 1146354-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Methanone,[4-[[3-(1H-1,2,4-triazol-5-yl)-5-(trifluoromethyl)phenyl]sulfonyl]-1-piperazinyl][(1R,2R)-2-[4-(trifluoromethyl)phenyl]cyclopropyl]-
• 英文别名: [4-[3-(1H-1,2,4-triazol-5-yl)-5-(trifluoromethyl)phenyl]sulfonylpiperazin-1-yl]-[(1R,2R)-2-[4-(trifluoromethyl)phenyl]cyclopropyl]methanone
• CAS: 1146354-35-9
• 化学式: C₂₄H₂₁F₆N₅O₃S
• 分子量: 573.519
• InChiKey: KHBYHUBFGVKELV-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3-(trifluoromethyl)-5-[4-[(1R,2R)-2-[4-(trifluoromethyl)phenyl]cyclopropanecarbonyl]piperazin-1-yl]sulfonylbenzonitrile 、 甲酰肼 在 1-甲基吡咯烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以81%的产率得到Methanone,[4-[[3-(1H-1,2,4-triazol-5-yl)-5-(trifluoromethyl)phenyl]sulfonyl]-1-piperazinyl][(1R,2R)-2-[4-(trifluoromethyl)phenyl]cyclopropyl]-
  参考文献：
  名称：

  1-Sulfonyl-4-acylpiperazines as Selective Cannabinoid-1 Receptor (CB1R) Inverse Agonists for the Treatment of Obesity

  摘要：

  A novel series of 1-sulfonyl-4-acylpiperazines as selective cannabinoid-1 receptor (CB1R) inverse agonists was discovered through high throughput screening (HTS) and medicinal chemistry lead optimization. Potency and in vivo properties were systematically optimized to afford orally bioavailable, highly efficacious, and selective CB1R inverse agonists that caused food intake suppression and body weight reduction in diet-induced obese rats and dogs. It was found that the receptor binding assay predicted in vivo efficacy better than functional antagonist/inverse agonist activities. This observation expedited the structure-activity relationship (SAR) analysis and may have implications beyond the series Of Compounds presented herein.

  DOI：

  10.1021/jm900063x