(3aR,4R,9bS)-4-(2,4-dichlorophenyl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-8-carboxylic acid

• 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,4R,9bS)-4-(2,4-dichlorophenyl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-8-carboxylic acid
• 化学式: C₁₉H₁₅Cl₂NO₂
• 分子量: 360.24
• InChiKey: DLSUYVWZOWUVHV-VEVIJQCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aR,4R,9bS)-4-(2,4-dichlorophenyl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-8-carboxylic acid 、 甲氧基胺盐酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到(3aS,4S,9bR)-4-(2,4-dichlorophenyl)-N-methoxy-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-8-carboxamide
  参考文献：
  名称：

  Structure–activity relationship (SAR) investigations of tetrahydroquinolines as BKCa agonists

  摘要：

  The membrane bound large-conductance, calcium-activated potassium channel (BKCa) is an important regulator of neuronal activity. Here we describe the identification and structure-activity relationship of a novel class of potent tetrahydroquinoline BKCa agonists. An example from this class of BKCa agonists was shown to depress the spontaneous neuronal discharges in an electrophysiological model of migraine. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.125
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 反应 2.0h， 生成 (3aR,4R,9bS)-4-(2,4-dichlorophenyl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-8-carboxylic acid
  参考文献：
  名称：

  Structure–activity relationship (SAR) investigations of tetrahydroquinolines as BKCa agonists

  摘要：

  The membrane bound large-conductance, calcium-activated potassium channel (BKCa) is an important regulator of neuronal activity. Here we describe the identification and structure-activity relationship of a novel class of potent tetrahydroquinoline BKCa agonists. An example from this class of BKCa agonists was shown to depress the spontaneous neuronal discharges in an electrophysiological model of migraine. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.125