(3aR,4S,9bS)-4-(4-bromophenyl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-8-sulfonamide | 1476807-74-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (3aR,4S,9bS)-4-(4-bromophenyl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-8-sulfonamide
• 英文别名: GAT107
• CAS: 1476807-74-5
• 化学式: C₁₈H₁₇BrN₂O₂S
• 分子量: 405.315
• InChiKey: YNCXHXYZTLIZTO-HDMKZQKVSA-N

物化性质

• 沸点：
  566.2±60.0 °C(Predicted)
• 密度：
  1.505±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  环戊二烯 、 对溴苯甲醛 、 磺胺 在 indium(III) chloride 作用下， 以 乙腈 、 乙醇 、 正己醇 为溶剂， 反应 0.25h， 以99.02%的产率得到
  参考文献：
  名称：

  Expeditious Synthesis, Enantiomeric Resolution, and Enantiomer Functional Characterization of (4-(4-Bromophenyl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-8-sulfonamide (4BP-TQS): An Allosteric Agonist-Positive Allosteric Modulator of α7 Nicotinic Acetylcholine Receptors

  摘要：

  An expeditious microwave-assisted synthesis of 4BP-TQS, its enantiomeric separation, and their functional evaluation is reported. Electrophysiological characterization in Xenopus oocytes revealed that activity exclusively resided in the (+)-enantiomer 1b (GAT107) and (-)-enantiomer 1a did not affect its activity when coapplied. X-ray crystallography studies revealed the absolute stereochemistry of 1b to be 3aR,4S,9bS. 1b represents the most potent ago-PAM of alpha 7 nAChRs available to date and is considered for further in vivo evaluation.

  DOI：

  10.1021/jm401267t

文献信息

• LIGANDS FOR ALPHA-7 NICOTINIC ACETYLCHOLINE RECEPTORS AND METHODS OF TREATING NEUROLOGICAL AND INFLAMMATORY CONDITIONS
  申请人：Northeastern University

  公开号：EP3180086A1

  公开（公告）日：2017-06-21
• Ligands for Alpha-7 Nicotinic Acetylcholine Receptors and Methods of Treating Neurological and Inflammatory Conditions
  申请人：Northeastern University

  公开号：US20170217984A1

  公开（公告）日：2017-08-03

  Compounds are provided which bind to an allosteric site on the mammalian alpha-7 nicotinic acetylcholine receptor (alpha-7 nAChR) and act as positive allosteric modulators with or without allosteric agonist activity. The compounds are useful in diagnosing, preventing, or treating a variety of disorders involving cognition, learning, memory, neurodegeneration, drug addiction, inflammation, chronic pain, and neuropathic pain. The compounds also can be used to enhance memory and learning in normal individuals.
• [EN] LIGANDS FOR ALPHA-7 NICOTINIC ACETYLCHOLINE RECEPTORS AND METHODS OF TREATING NEUROLOGICAL AND INFLAMMATORY CONDITIONS<br/>[FR] LIGANDS POUR LA SOUS-UNITÉ ALPHA-7 DES RÉCEPTEURS NICOTINIQUES DE L'ACÉTYLCHOLINE ET MÉTHODES DE TRAITEMENT DE TROUBLES NEUROLOGIQUES ET INFLAMMATOIRES
  申请人：UNIV NORTHEASTERN

  公开号：WO2016014847A1

  公开（公告）日：2016-01-28

  Compounds are provided which bind to an allosteric site on the mammalian alpha-7 nicotinic acetylcholine receptor (alpha-7 nAChR) and act as positive allosteric modulators with or without allosteric agonist activity. The compounds are useful in diagnosing, preventing, or treating a variety of disorders involving cognition, learning, memory, neurodegeneration, drug addiction, inflammation, chronic pain, and neuropathic pain. The compounds also can be used to enhance memory and learning in normal individuals.