1H-Imidazole-4-carboxylic acid, 1-[2-(2-chlorophenyl)ethyl]- | 1295542-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1H-Imidazole-4-carboxylic acid, 1-[2-(2-chlorophenyl)ethyl]-
• 英文别名: 1-[2-(2-chlorophenyl)ethyl]imidazole-4-carboxylic acid
• CAS: 1295542-33-4
• 化学式: C₁₂H₁₁ClN₂O₂
• 分子量: 250.685
• InChiKey: PCRMGRKVMVMIMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.12
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1H-Imidazole-4-carboxylic acid, 1-[2-(2-chlorophenyl)ethyl]- 、 N-甲基-3-氨基吡唑 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 1-(2-chlorophenethyl)-N-(1-methyl-1H-pyrazol-3-yl)-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
• 作为产物：
  描述：

  在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1H-Imidazole-4-carboxylic acid, 1-[2-(2-chlorophenyl)ethyl]-
  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