N-(1-methyl-1H-pyrazol-3-yl)-1-(3-(trifluoromethoxy)benzyl)-1H-imidazole-4-carboxamide | 1295541-89-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(1-methyl-1H-pyrazol-3-yl)-1-(3-(trifluoromethoxy)benzyl)-1H-imidazole-4-carboxamide
• 英文别名: N-(1-methylpyrazol-3-yl)-1-[[3-(trifluoromethoxy)phenyl]methyl]imidazole-4-carboxamide
• CAS: 1295541-89-7
• 化学式: C₁₆H₁₄F₃N₅O₂
• 分子量: 365.315
• InChiKey: RLIOGLONFBOCIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  74
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 水 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 生成 N-(1-methyl-1H-pyrazol-3-yl)-1-(3-(trifluoromethoxy)benzyl)-1H-imidazole-4-carboxamide
  参考文献：
  名称：

  N-Benzylimidazole carboxamides as potent, orally active stearoylCoA desaturase-1 inhibitors

  摘要：

  A potent, small molecule inhibitor with a favorable pharmacokinetic profile to allow for sustained SCD inhibition in vivo was identified. Starting from a low MW acyl guanidine (5a), identified with a RapidFire High-Throughput Mass Spectrometry (RF-MS) assay, iterative library design was used to rapidly probe the amide and tail regions of the molecule. Singleton synthesis was used to probe core changes. Biological evaluation of a SCD inhibitor (5b) included in vitro potency at SCD-1 and in vivo modulation of the plasma desaturation index (DI) in rats on a low essential fatty acid (LEFA) diet. In addition to dose-dependent decrease in DI, effects on rodent ocular tissue were noted. Therefore, in rat, these SCD inhibitors only recapitulate a portion of phenotype exhibited by the SCD-1 knockout mouse. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.113

文献信息

• N-Benzylimidazole carboxamides as potent, orally active stearoylCoA desaturase-1 inhibitors
  作者：Karen A. Atkinson、Elena E. Beretta、Janice A. Brown、Mayda Castrodad、Yue Chen、Judith M. Cosgrove、Ping Du、John Litchfield、Michael Makowski、Kelly Martin、Thomas J. McLellan、Constantin Neagu、David A. Perry、David W. Piotrowski、Claire M. Steppan、Richard Trilles

  DOI：10.1016/j.bmcl.2011.01.113

  日期：2011.3

  A potent, small molecule inhibitor with a favorable pharmacokinetic profile to allow for sustained SCD inhibition in vivo was identified. Starting from a low MW acyl guanidine (5a), identified with a RapidFire High-Throughput Mass Spectrometry (RF-MS) assay, iterative library design was used to rapidly probe the amide and tail regions of the molecule. Singleton synthesis was used to probe core changes. Biological evaluation of a SCD inhibitor (5b) included in vitro potency at SCD-1 and in vivo modulation of the plasma desaturation index (DI) in rats on a low essential fatty acid (LEFA) diet. In addition to dose-dependent decrease in DI, effects on rodent ocular tissue were noted. Therefore, in rat, these SCD inhibitors only recapitulate a portion of phenotype exhibited by the SCD-1 knockout mouse. (C) 2011 Elsevier Ltd. All rights reserved.