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

中文名称
——
中文别名
——
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
(3aR,4S,9bS)-4-(4-bromophenyl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-8-sulfonamide化学式
CAS
1476807-74-5
化学式
C18H17BrN2O2S
mdl
——
分子量
405.315
InChiKey
YNCXHXYZTLIZTO-HDMKZQKVSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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
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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.
  • Expeditious Synthesis, Enantiomeric Resolution, and Enantiomer Functional Characterization of (4-(4-Bromophenyl)-3a,4,5,9b-tetrahydro-3<i>H</i>-cyclopenta[<i>c</i>]quinoline-8-sulfonamide (4BP-TQS): An Allosteric Agonist-Positive Allosteric Modulator of α7 Nicotinic Acetylcholine Receptors
    作者:Ganesh A. Thakur、Abhijit R. Kulkarni、Jeffrey R. Deschamps、Roger L. Papke
    DOI:10.1021/jm401267t
    日期:2013.11.14
    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.
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