3-(2,2,3,3-tetramethyl-cyclopropanecarbonyl)-1H-indole-6-carbonitrile | 895157-57-0

• 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: 3-(2,2,3,3-tetramethyl-cyclopropanecarbonyl)-1H-indole-6-carbonitrile
• 英文别名: 3-(2,2,3,3-tetramethylcyclopropanecarbonyl)-1H-indole-6-carbonitrile
• CAS: 895157-57-0
• 化学式: C₁₇H₁₈N₂O
• 分子量: 266.343
• InChiKey: OZUPQIPLEAPAGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  56.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2,2,3,3-tetramethyl-cyclopropanecarbonyl)-1H-indole-6-carbonitrile 、 (4-(羟基甲基)-四氢-2H-吡喃-4-基)甲烷磺酸盐 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以0.87%的产率得到1-(tetrahydro-2H-pyran-4-ylmethyl)-3-[(2,2,3,3-tetramethylcyclopropyl)carbonyl]-1H-indole-6-carbonitrile
  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
• 作为产物：
  描述：

  6-氰基吲哚 、 2,2,3,3-四甲基环丙烷羧酸酰氯 在 乙基溴化镁 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙醚 为溶剂， 以0.91 g的产率得到3-(2,2,3,3-tetramethyl-cyclopropanecarbonyl)-1H-indole-6-carbonitrile
  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

• Indoles are cannabinoid receptor ligands
  申请人：Abbott Laboratories

  公开号：US07750039B2

  公开（公告）日：2010-07-06

  The present invention provides novel compounds of Formula (I) which are CB2 selective ligands useful for the treatment of pain.

  本发明提供了一种新型的化合物（I），它们是CB2选择性配体，可用于治疗疼痛。
• 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