(2,5-dimethyl-1H-pyrrol-3-yl)(naphthalen-1-yl)methanone | 24835-87-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2,5-dimethyl-1H-pyrrol-3-yl)(naphthalen-1-yl)methanone
• 英文别名: (2,5-dimethyl-1H-pyrrol-3-yl)-naphthalen-1-ylmethanone
• CAS: 24835-87-8
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: WFVIUAODRZDGNO-UHFFFAOYSA-N

物化性质

• 沸点：
  436.4±33.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  32.86
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (2,5-dimethyl-1H-pyrrol-3-yl)(naphthalen-1-yl)methanone 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 作用下， 以 1,4-二氧六环 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (4-Bromo-2,5-dimethyl-1-pentyl-1H-pyrrol-3-yl)-naphthalen-1-yl-methanone
  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 、 1-萘甲酰氯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 以39%的产率得到(2,5-dimethyl-1H-pyrrol-3-yl)(naphthalen-1-yl)methanone
  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