1-(5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1-methyl-1H-pyrrole-2-carbonyl)-4-phenylpiperidine-4-carboxamide | 1243243-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1-methyl-1H-pyrrole-2-carbonyl)-4-phenylpiperidine-4-carboxamide
• 英文别名: 1-[5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1-methylpyrrole-2-carbonyl]-4-phenylpiperidine-4-carboxamide
• CAS: 1243243-18-6
• 化学式: C₃₀H₂₆Cl₃N₃O₂
• 分子量: 566.914
• InChiKey: JKASSHYCBFCQEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1-methyl-1H-pyrrole-2-carboxylic acid 、 4-carbamoyl-4-phenylpiperidine 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1-methyl-1H-pyrrole-2-carbonyl)-4-phenylpiperidine-4-carboxamide
  参考文献：
  名称：

  Rational design of a novel peripherally-restricted, orally active CB1 cannabinoid antagonist containing a 2,3-diarylpyrrole motif

  摘要：

  A new series of 2,3-diarylpyrroles have been prepared and evaluated as CB1 antagonists. Modulation of the topological polar surface area allowed the identification of high affinity peripherally-restricted CB1 antagonists. Compound 11, obtained after further optimization of the metabolic profile displayed very low brain penetration, yet was able to reverse CP55940-induced gastrointestinal transit inhibition following oral administration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.017

文献信息

• Rational design of a novel peripherally-restricted, orally active CB1 cannabinoid antagonist containing a 2,3-diarylpyrrole motif
  作者：Laurent Hortala、Murielle Rinaldi-Carmona、Christian Congy、Laurent Boulu、Freddy Sadoun、Gérard Fabre、Olivier Finance、Francis Barth

  DOI：10.1016/j.bmcl.2010.06.017

  日期：2010.8

  A new series of 2,3-diarylpyrroles have been prepared and evaluated as CB1 antagonists. Modulation of the topological polar surface area allowed the identification of high affinity peripherally-restricted CB1 antagonists. Compound 11, obtained after further optimization of the metabolic profile displayed very low brain penetration, yet was able to reverse CP55940-induced gastrointestinal transit inhibition following oral administration. (C) 2010 Elsevier Ltd. All rights reserved.