(-)-N¹-noreseroline | 6785-93-9

• 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: (-)-N¹-noreseroline
• 英文别名: (3aR,8bS)-4,8b-dimethyl-1,2,3,3a-tetrahydropyrrolo[2,3-b]indol-7-ol
• CAS: 6785-93-9
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: FFIJQGXPIZOIHM-NEPJUHHUSA-N

物化性质

• 沸点：
  382.4±42.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-methoxy-8-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole 在 三溴化硼 作用下， 以 氯仿 为溶剂， 反应 72.0h， 生成 (-)-N¹-noreseroline
  参考文献：
  名称：

  Comparison of (-)-eseroline with (+)-eseroline and dihydroseco analogs in antinociceptive assays: confirmation of rubreserine structure by x-ray analysis

  摘要：

  The enantiomers of eseroline bind to opiate receptors of rat brain membranes with equal affinities and show opiate agonist properties as inhibitors of adenylate cyclase in vitro. However, only (-)-eseroline shows potent narcotic agonist activity in vivo, similar to that of morphine. Neither (-)-noreseroline, (+)-eseroline, nor the open dihydroseco analogue (-)-8 shows analgetic effects in vivo. The structure of rubreserine being a resonance hybrid of an o-quinone with its zwitterionic mesomer is confirmed by solid-state X-ray diffraction analysis.

  DOI：

  10.1021/jm00161a023

文献信息

• Carbamoyl esters that inhibit cholinesterase and release pharmacologically active agents
  申请人：CoLucid Pharmaceuticals, Inc.

  公开号：EP2314571A2

  公开（公告）日：2011-04-27

  Carbamoyl esters inhibit cholinesterase activity and upon hydrolysis release a pharmacologically active agent. The carbamoyl esters are employed in methods to treat an individual. The pharmacologically active agent obtained by hydrolysis of the carbamoyl treat for example,a nervous system condition, cholinergie deficiency and conditions or diseases associated with a deficiency in a pharmacologically active agent such as acetylcholine.

  氨基甲酰基酯可抑制胆碱酯酶的活性，并在水解后释放出具有药理活性的药剂。氨基甲酰基酯可用于治疗疾病。通过水解氨基甲酰基获得的药理活性剂可治疗神经系统疾病、胆碱酯酶缺乏症以及与乙酰胆碱等药理活性剂缺乏有关的疾病。
• Comparison of (-)-eseroline with (+)-eseroline and dihydroseco analogs in antinociceptive assays: confirmation of rubreserine structure by x-ray analysis
  作者：Bernhard Schonenberger、Arthur E. Jacobson、Arnold Brossi、Richard Streaty、Werner A. Klee、Judith L. Flippen-Anderson、Richard Gilardi

  DOI：10.1021/jm00161a023

  日期：1986.11

  The enantiomers of eseroline bind to opiate receptors of rat brain membranes with equal affinities and show opiate agonist properties as inhibitors of adenylate cyclase in vitro. However, only (-)-eseroline shows potent narcotic agonist activity in vivo, similar to that of morphine. Neither (-)-noreseroline, (+)-eseroline, nor the open dihydroseco analogue (-)-8 shows analgetic effects in vivo. The structure of rubreserine being a resonance hybrid of an o-quinone with its zwitterionic mesomer is confirmed by solid-state X-ray diffraction analysis.