N-(furan-2-ylmethyl)-N-phenethyl-4-(4-(trifluoromethoxy)phenyl)-1H-1,2,3-triazole-1-carboxamide | 1476719-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(furan-2-ylmethyl)-N-phenethyl-4-(4-(trifluoromethoxy)phenyl)-1H-1,2,3-triazole-1-carboxamide
• 英文别名: N-(furan-2-ylmethyl)-N-(2-phenylethyl)-4-[4-(trifluoromethoxy)phenyl]triazole-1-carboxamide
• CAS: 1476719-67-1
• 化学式: C₂₃H₁₉F₃N₄O₃
• 分子量: 456.424
• InChiKey: KZMPJUCRJDYAJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  呋喃-2-甲基-苯乙胺 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 N-(furan-2-ylmethyl)-N-phenethyl-4-(4-(trifluoromethoxy)phenyl)-1H-1,2,3-triazole-1-carboxamide
  参考文献：
  名称：

  Development and Optimization of Piperidyl-1,2,3-Triazole Ureas as Selective Chemical Probes of Endocannabinoid Biosynthesis

  摘要：

  We have previously shown that 1,2,3-triazole ureas (1,2,3-TUs) act as versatile class of irreversible serine hydrolase inhibitors that can be tuned to create selective probes for diverse members of this large enzyme class, including diacylglycerol lipase-beta (DAGL beta), a principal biosynthetic enzyme for the endocannabinoid 2-arachidonoylglycerol (2-AG). Here, we provide a detailed account of the discovery, synthesis, and structure-activity relationship (SAR) of (2-substituted)-piperidyl-1,2,3-TUs that selectively inactivate DAGL beta in living systems. Key to success was the use of activity-based protein profiling (ABPP) with broad-spectrum and tailored activity-based probes to guide our medicinal chemistry efforts. We also describe an expanded repertoire of DAGL-tailored activity-based probes that includes biotinylated and alkyne agents for enzyme enrichment coupled with mass spectrometry-based proteomics and assessment of proteome-wide selectivity. Our findings highlight the broad utility of 1,2,3-TUs for serine hydrolase inhibitor development and their application to create selective probes of endocannabinoid biosynthetic pathways.

  DOI：

  10.1021/jm400898x