3-[4-(2-cyclobutylcarbonylaminoethyl)-6-methoxynaphth-2-yl]benzoic acid methyl ester | 686319-60-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-[4-(2-cyclobutylcarbonylaminoethyl)-6-methoxynaphth-2-yl]benzoic acid methyl ester
• 英文别名: Methyl 3-(4-{2-[(cyclobutylcarbonyl)amino]ethyl}-6-methoxy-2-naphthyl)-benzoate；Methyl 3-[4-[2-(cyclobutanecarbonylamino)ethyl]-6-methoxynaphthalen-2-yl]benzoate
• CAS: 686319-60-8
• 化学式: C₂₆H₂₇NO₄
• 分子量: 417.505
• InChiKey: YUYLBWQOGQEMTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[4-(2-cyclobutylcarbonylaminoethyl)-6-methoxynaphth-2-yl]benzoic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.0h， 以40%的产率得到N-(2-{3-[3-(Hydroxymethyl)phenyl]-7-methoxy-1-naphthyl}ethyl)-cyclobutanecarboxamide
  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
• 作为产物：
  描述：

  N-[2-(3-bromo-7-methoxynaphth-1-yl)ethyl]cyclobutylcarboxamide 、 3-甲氧基羰基苯硼酸 在 palladium diacetate 四丁基溴化铵 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 以43%的产率得到3-[4-(2-cyclobutylcarbonylaminoethyl)-6-methoxynaphth-2-yl]benzoic acid methyl ester
  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

• Phenylnaphthalene compounds
  申请人：Poissonnier-Durieux Sophie

  公开号：US20060106111A1

  公开（公告）日：2006-05-18

  The invention relates to compounds of formula (I): wherein: A represents R 3 represents alkoxy, R 4 is as defined in the description, p is 1, 2 or 3, and medicinal products containing the same which are useful in treating or preventing melatoninergic disorders.

  该发明涉及以下化合物的结构（I）： 其中： A代表 R3代表烷氧基， R4如描述中定义， p为1、2或3， 以及含有这些化合物的药物，用于治疗或预防褪黑素失调疾病。
• 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.