[2-methyl-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)methanone | 895157-72-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: [2-methyl-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)methanone
• 英文别名: 4-(2-{2-methyl-3-[(2,2,3,3-tetramethylcyclopropyl)carbonyl]-1H-indol-1-yl}ethyl)morpholine；[2-methyl-1-(2-morpholin-4-ylethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone
• CAS: 895157-72-9
• 化学式: C₂₃H₃₂N₂O₂
• 分子量: 368.519
• InChiKey: KHIQQNMDIZNDBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [2-methyl-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)methanone 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以53%的产率得到[2-methyl-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)methanone hydrochloride
  参考文献：
  名称：

  WO2006/69196

  摘要：

  公开号：
• 作为产物：
  描述：

  (2-methyl-1H-indol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone 、 4-(2-甲烷磺酰氧基乙基)吗啉 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以0.25 g的产率得到[2-methyl-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)methanone
  参考文献：
  名称：

  Indol-3-yl-tetramethylcyclopropyl Ketones: Effects of Indole Ring Substitution on CB₂ Cannabinoid Receptor Activity

  摘要：

  A series of potent indol-3-yl-tetramethylcyclopropyl ketones have been prepared as CB(2) cannabinoid receptor ligands. Two unsubstituted indoles (5, 32) were the starting points for an investigation of the effect of indole ring substitutions on CB(2) and CB, binding affinities and activity in a CB(2) in vitro functional assay. Indole ring substitutions had varying effects on CB(2) and CB(1) binding, but were generally detrimental to agonist activity. Substitution on the indole ring did lead to improved CB(2)/CB(1) binding selectivity in some cases (i.e., 7-9, 15-20). All indoles with the morpholino-ethyl side chain (32-43) exhibited weaker binding affinity and less agonist activity relative to that of their tetrahydropyranyl-methyl analogs (5-31). Several agonists were active in the complete Freund's adjuvant model of chronic inflammatory thermal hyperalgesia (32, 15).

  DOI：

  10.1021/jm7011613

文献信息

• NOVEL INDOLES ARE CANNABINOID RECEPTOR LIGANDS
  申请人：Frost Jennifer M.

  公开号：US20110065685A1

  公开（公告）日：2011-03-17

  The present invention provides novel compounds of Formula (I) which are CB 2 selective ligands useful for the treatment of pain.

  本发明提供了式（I）的新化合物，它们是CB2选择性配体，可用于治疗疼痛。
• 3-CYCLOALKYLCARBONYL INDOLES AS CANNABINOID RECEPTOR LIGANDS
  申请人：AbbVie Inc.

  公开号：EP1833824B1

  公开（公告）日：2016-08-03
• Novel indoles are cannabinoid receptor ligands
  申请人：Frost M. Jennifer

  公开号：US20070037801A1

  公开（公告）日：2007-02-15

  The present invention provides novel compounds of Formula (I) which are CB 2 selective ligands useful for the treatment of pain.
• US7560481B2
  申请人：——

  公开号：US7560481B2

  公开（公告）日：2009-07-14
• [EN] 3-CYCLOALKYLCARBONYL INDOLES AS CANNABINOID RECEPTOR LIGANDS<br/>[FR] 3-CYCLOALKYLCARBONYL INDOLES UTILISES COMME LIGANDS DES RECEPTEURS CANNABINOIDES
  申请人：ABBOTT LAB

  公开号：WO2006069196A1

  公开（公告）日：2006-06-29

  [EN] The present invention provides novel compounds of Formula (I), which are CB₂ selective ligands useful for the treatment of pain.
  [FR] La présente invention concerne de nouveaux composés représentés par la formule générale (I) qui sont des ligands sélectifs des CB₂, destinés au traitement de la douleur.