N-[2-(7-methoxynaphth-1-yl)ethyl]monofluoroacetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[2-(7-methoxynaphth-1-yl)ethyl]monofluoroacetamide
• 英文别名: 2-fluoro-N-(2-(7-methoxynaphthalen-1-yl)ethyl)acetamide；fluoroacetamidoagomelatine；2-fluoro-N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide
• 化学式: C₁₅H₁₆FNO₂
• 分子量: 261.296
• InChiKey: JCYKAJRXJDQCLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴-N-[2-(7-甲氧基萘-1-基)乙基]乙酰胺 在 potassium fluoride 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以26%的产率得到N-[2-(7-methoxynaphth-1-yl)ethyl]monofluoroacetamide
  参考文献：
  名称：

  Neu; Niles; Brough, Medicinal Chemistry Research, 2000, vol. 10, # 2, p. 114 - 121

  摘要：

  DOI：

文献信息

• Radiosynthesis and <i>In Vivo</i> Evaluation of Four Positron Emission Tomography Tracer Candidates for Imaging of Melatonin Receptors
  作者：Hussein Bdair、Thomas A. Singleton、Karen Ross、Dean Jolly、Min Su Kang、Arturo Aliaga、Marius Tuznik、Tanpreet Kaur、Saïd Yous、Jean-Paul Soucy、Gassan Massarweh、Peter J. H. Scott、Robert Koeppe、Gilberto Spadoni、Annalida Bedini、David A. Rudko、Gabriella Gobbi、Chawki Benkelfat、Pedro Rosa-Neto、Allen F. Brooks、Alexey Kostikov

  DOI：10.1021/acschemneuro.1c00678

  日期：2022.5.4

  therapeutic target for new pharmacological interventions in the treatment of sleep and mood disorders; thus, imaging tools to further investigate its role in the brain are highly sought-after. We aimed to develop selective radiotracers for in vivo imaging of both MT1 and MT2 by positron emission tomography (PET). We identified four previously reported MT ligands with picomolar affinities to the target based

  褪黑激素是一种神经激素，通过激活褪黑激素受体 1 型和 2 型（MT 1和 MT 2）来调节哺乳动物的多种生理功能。褪黑激素能系统是治疗睡眠和情绪障碍的新药理学干预的新兴治疗靶点；因此，进一步研究其在大脑中作用的成像工具非常受欢迎。我们的目标是开发选择性放射性示踪剂，用于通过正电子发射断层扫描 (PET)对 MT 1和 MT 2进行体内成像。我们根据不同的支架鉴定了四种先前报道的对靶标具有皮摩尔亲和力的 MT 配体，这些支架也适用于碳 11 或氟 18 的放射性标记。[11 C]UCM765、[ 11 C]UCM1014、[ 18 F]3-fluoroagomelatine ([ 18 F]3FAGM) 和 [ 18 F]fluoroacetamidoagomelatine ([ 18 F]FAAGM) 以高放射化学纯度合成并在野外进行了评估型大鼠。所有四种示踪剂在大鼠中显示出中等至高的脑
• Design, synthesis and pharmacological evaluation of new series of naphthalenic analogues as melatoninergic (MT1/MT2) and serotoninergic 5-HT2C dual ligands (I)
  作者：Mohamed Ettaoussi、Ahmed Sabaouni、Marouan Rami、Jean A. Boutin、Philippe Delagrange、Pierre Renard、Michael Spedding、Daniel-Henri Caignard、Pascal Berthelot、Saïd Yous

  DOI：10.1016/j.ejmech.2012.01.027

  日期：2012.3

  As part of our ongoing interest in developing new melatoninergic ligands bearing the same pharmacological profile as agomelatine, we focused our attention on this compound as a lead. Several chemical modifications have been performed on positions C-3 and 8 of the naphthalene ring determined as primary targets for the agomelatine metabolism. Herein we report the modulation of the positions C-3 and 7 in addition of the amide side chain because of this later prominent role in the affinity profile of such ligands. Synthesized compounds were then biologically evaluated at human cloned melatoninergic and serotoninergic receptors and showed different binding affinity and intrinsic activity profiles. Compounds bearing fluoroacetamide group (compounds 4 and 5) showed a high melatoninergic binding affinity particularly towards MT1 receptor subtype. Thus, the fluoroacetamide 4 exhibited a good melatoninergic (mT(1)/MT2) binding affinity (70 pm) higher than the lead. Moreover, other compounds (10a, 10e, 16, 17 and 18) issued from these modulations behaved as MT1 and MT2 agonists and exhibited a sub-nanomolar binding affinity towards these receptors. However, only compounds 10e, 17 and 18 showed a sub-nanomolar binding affinity at 5-HT2C higher than the agomelatine. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Neu; Niles; Brough, Medicinal Chemistry Research, 2000, vol. 10, # 2, p. 114 - 121
  作者：Neu、Niles、Brough、Chen、Snieckus、Firnau

  DOI：——

  日期：——