N-[2-(3-(3-Ethoxycarbonylaminophenyl)-7-methoxynaphth-1-yl)ethyl]acetamide | 1069120-49-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[2-(3-(3-Ethoxycarbonylaminophenyl)-7-methoxynaphth-1-yl)ethyl]acetamide
• 英文别名: ethyl N-[3-[4-(2-acetamidoethyl)-6-methoxynaphthalen-2-yl]phenyl]carbamate
• CAS: 1069120-49-5
• 化学式: C₂₄H₂₆N₂O₄
• 分子量: 406.481
• InChiKey: UEKXNAQNOCLRRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  S24773 hydrochloride 、 氯甲酸乙酯 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以70%的产率得到N-[2-(3-(3-Ethoxycarbonylaminophenyl)-7-methoxynaphth-1-yl)ethyl]acetamide
  参考文献：
  名称：

  Synthesis of 3-phenylnaphthalenic derivatives as new selective MT2 melatoninergic ligands

  摘要：

  A series of naphthalenic analogues of melatonin were prepared and evaluated as melatonin receptor MT(2) selective ligands. Activity and MT(2) selectivity can be modulated with suitable variations of the C-3 phenyl and the acyl group on the C-1 side chain. Surprisingly, in contrast with what had been previously described in other series (2-benzylindoles, 2-benzylbenzofurans and 3-phenyltetralins), the presence of a C-3 phenyl with a functional group on the meta position seems to be primordial for MT2 afinity and selectivity. Indeed,N-[2-( 3-(3-hydroxymethylphenyl)-7-methoxynaphth-1-yl) ethyl] acetamide (21) is one of the best MT(2) selective ligands described until now and behaves as an antagonist. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.052

文献信息

• Synthesis of 3-phenylnaphthalenic derivatives as new selective MT2 melatoninergic ligands
  作者：Sophie Poissonnier-Durieux、Mohamed Ettaoussi、Basile Pérès、Jean A. Boutin、Valérie Audinot、Caroline Bennejean、Philippe Delagrange、Daniel Henri Caignard、Pierre Renard、Pascal Berthelot、Daniel Lesieur、Saïd Yous

  DOI：10.1016/j.bmc.2008.08.052

  日期：2008.9

  A series of naphthalenic analogues of melatonin were prepared and evaluated as melatonin receptor MT(2) selective ligands. Activity and MT(2) selectivity can be modulated with suitable variations of the C-3 phenyl and the acyl group on the C-1 side chain. Surprisingly, in contrast with what had been previously described in other series (2-benzylindoles, 2-benzylbenzofurans and 3-phenyltetralins), the presence of a C-3 phenyl with a functional group on the meta position seems to be primordial for MT2 afinity and selectivity. Indeed,N-[2-( 3-(3-hydroxymethylphenyl)-7-methoxynaphth-1-yl) ethyl] acetamide (21) is one of the best MT(2) selective ligands described until now and behaves as an antagonist. (C) 2008 Elsevier Ltd. All rights reserved.