1,3-dicyclohexyl-2-(2,5-dimethyl-1-pentyl-1H-pyrrole-3-carbonyl)isourea | 643744-43-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1,3-dicyclohexyl-2-(2,5-dimethyl-1-pentyl-1H-pyrrole-3-carbonyl)isourea
• CAS: 643744-43-8
• 化学式: C₂₅H₄₁N₃O₂
• 分子量: 415.619
• InChiKey: MEACAVZLCXZFSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.06
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  55.62
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,3-dicyclohexyl-2-(2,5-dimethyl-1-pentyl-1H-pyrrole-3-carbonyl)isourea 在 三乙胺 作用下， 以 xylene 为溶剂， 反应 15.0h， 以0.066 g的产率得到2,5-dimethyl-1-pentyl-1H-pyrrole-3-carboxylic acid cyclohexylamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of a series of pyrrole cannabinoid receptor agonists

  摘要：

  We designed and synthesized a series of pyrrole derivatives with the aim of investigating the structure-activity relationship (SAR) for the binding of non-classical agonists to CB1 and CB2 cannabinoid receptors. Superposition of two pyrrole-containing cannabinoid agonists, JWH-007 and JWH-161, allowed us to identify positions 1, 3 and 4 of the pyrrole nucleus as amenable to additional investigation. We prepared the 1-alkyl-2,5-dimethyl-3,4-substituted pyrroles 10a-e, 11a-d, 17, 21, 25 and the tetrahydroindole 15, and evaluated their ability to bind to and activate cannabinoid receptors. Noteworthy in this set of compounds are the 4-bromopyrrole 11a, which has an affinity for CB1 and CB2 receptors comparable to that of well-characterized heterocyclic cannabimimetics such as Win-55,212-2; the amide 25, which, although possessing a moderate affinity for cannabinoid receptors, demonstrates that the 3-naphthoyl group, commonly present in indole and pyrrole cannabimimetics, can be substituted by alternative moieties; and compounds 10d, 11d, showing CB1 partial agonist properties. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00413-9
• 作为产物：
  描述：

  2,5-二甲基吡咯-3-乙酯 在 lithium hydroxide 、 邻氨基苯乙酮 、 sodium hydride 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1,3-dicyclohexyl-2-(2,5-dimethyl-1-pentyl-1H-pyrrole-3-carbonyl)isourea
  参考文献：
  名称：

  Synthesis and structure–activity relationships of a series of pyrrole cannabinoid receptor agonists

  摘要：

  We designed and synthesized a series of pyrrole derivatives with the aim of investigating the structure-activity relationship (SAR) for the binding of non-classical agonists to CB1 and CB2 cannabinoid receptors. Superposition of two pyrrole-containing cannabinoid agonists, JWH-007 and JWH-161, allowed us to identify positions 1, 3 and 4 of the pyrrole nucleus as amenable to additional investigation. We prepared the 1-alkyl-2,5-dimethyl-3,4-substituted pyrroles 10a-e, 11a-d, 17, 21, 25 and the tetrahydroindole 15, and evaluated their ability to bind to and activate cannabinoid receptors. Noteworthy in this set of compounds are the 4-bromopyrrole 11a, which has an affinity for CB1 and CB2 receptors comparable to that of well-characterized heterocyclic cannabimimetics such as Win-55,212-2; the amide 25, which, although possessing a moderate affinity for cannabinoid receptors, demonstrates that the 3-naphthoyl group, commonly present in indole and pyrrole cannabimimetics, can be substituted by alternative moieties; and compounds 10d, 11d, showing CB1 partial agonist properties. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00413-9