N-(2-((3aR,9bS)-2,3,3a,4-tetrahydro-1H-cyclopenta[c]quinolin-5[9bH]-yl)ethyl)acetamide | 922731-18-8

• 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: N-(2-((3aR,9bS)-2,3,3a,4-tetrahydro-1H-cyclopenta[c]quinolin-5[9bH]-yl)ethyl)acetamide
• 英文别名: N-[2-[(3aR,9bS)-1,2,3,3a,4,9b-hexahydrocyclopenta[c]quinolin-5-yl]ethyl]acetamide
• CAS: 922731-18-8
• 化学式: C₁₆H₂₂N₂O
• 分子量: 258.363
• InChiKey: FEZQDFWPZITKBN-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-((3aR,9bS)-2,3,3a,4-tetrahydro-1H-cyclopenta[c]quinolin-5[9bH]-yl)ethyl)acetamide 在 硫酸 、 sodium hydroxide 、 盐酸 作用下， 以 水 、 甲苯 、 乙醚 为溶剂， 反应 2.0h， 生成 2-((3aR,9bS)-2,3,3a,4-tetrahydro-1H-cyclopenta[c]quinolin-5[9bH]-yl)ethanamine hydrochloride
  参考文献：
  名称：

  Imaging Evaluation of 5HT_2C Agonists, [¹¹C]WAY-163909 and [¹¹C]Vabicaserin, Formed by Pictet–Spengler Cyclization

  摘要：

  The serotonin subtype 2C (5HT(2C)) receptor is an emerging and promising drug target to treat several disorders of the human central nervous system. In this current report, two potent and selective 5HT(2C) full agonists, WAY-163909 (2) and vabicaserin (3), were radiolabeled with carbon-11 via Pictet-Spengler cyclization with [C-11]formaldehyde and used in positron emission tomography (PET) imaging. Reaction conditions were optimized to exclude the major source of isotope dilution caused by the previously unknown breakdown of N,N-dimethylformamide (DMF) to formaldehyde at high temperature under mildly acid conditions. In vivo PET imaging was utilized to evaluate the pharmacokinetics and distribution of the carbon-11 labeled 5HT(2C) agonists. Both radiolabeled molecules exhibit high blood-brain barrier (BBB) penetration and nonspecific binding, which was unaltered by preadministration of the unlabeled agonist. Our work demonstrates that Pictet-Spengler cyclization can be used to label drugs with carbon-11 to study their pharmacokinetics and for evaluation as PET radiotracers.

  DOI：

  10.1021/jm401802f
• 作为产物：
  描述：

  2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[c]quinoline 在 对甲苯磺酸 、 sodium hydroxide 作用下， 以 水 、 异丙醇 、 甲苯 为溶剂， 反应 5.08h， 生成 N-(2-((3aR,9bS)-2,3,3a,4-tetrahydro-1H-cyclopenta[c]quinolin-5[9bH]-yl)ethyl)acetamide
  参考文献：
  名称：

  Imaging Evaluation of 5HT_2C Agonists, [¹¹C]WAY-163909 and [¹¹C]Vabicaserin, Formed by Pictet–Spengler Cyclization

  摘要：

  The serotonin subtype 2C (5HT(2C)) receptor is an emerging and promising drug target to treat several disorders of the human central nervous system. In this current report, two potent and selective 5HT(2C) full agonists, WAY-163909 (2) and vabicaserin (3), were radiolabeled with carbon-11 via Pictet-Spengler cyclization with [C-11]formaldehyde and used in positron emission tomography (PET) imaging. Reaction conditions were optimized to exclude the major source of isotope dilution caused by the previously unknown breakdown of N,N-dimethylformamide (DMF) to formaldehyde at high temperature under mildly acid conditions. In vivo PET imaging was utilized to evaluate the pharmacokinetics and distribution of the carbon-11 labeled 5HT(2C) agonists. Both radiolabeled molecules exhibit high blood-brain barrier (BBB) penetration and nonspecific binding, which was unaltered by preadministration of the unlabeled agonist. Our work demonstrates that Pictet-Spengler cyclization can be used to label drugs with carbon-11 to study their pharmacokinetics and for evaluation as PET radiotracers.

  DOI：

  10.1021/jm401802f

文献信息

• Diazepinoquinolines, synthesis thereof, and intermediates thereto
  申请人：Megati Sreenivasulu

  公开号：US20070027142A1

  公开（公告）日：2007-02-01

  The present invention relates to methods for synthesizing compounds useful as 5HT 2C agonists or partial agonists, derivatives thereof, and to intermediates thereto.

  本发明涉及用作5HT2C激动剂或部分激动剂的化合物的合成方法，以及其衍生物和中间体。
• US7671196B2
  申请人：——

  公开号：US7671196B2

  公开（公告）日：2010-03-02