3-[4-(2-Acetylaminoethyl)-6-methoxynaphth-2-yl]benzoic acid methyl ester | 1069120-43-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-[4-(2-Acetylaminoethyl)-6-methoxynaphth-2-yl]benzoic acid methyl ester
• 英文别名: methyl 3-[4-(2-acetamidoethyl)-6-methoxynaphthalen-2-yl]benzoate
• CAS: 1069120-43-9
• 化学式: C₂₃H₂₃NO₄
• 分子量: 377.44
• InChiKey: VADTZBHHWHUOCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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-Acetylaminoethyl)-6-methoxynaphth-2-yl]benzoic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以86%的产率得到3-(4-(2-Acetylaminoethyl)-6-methoxynaphth-2-yl)benzoic acid
  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]acetamide 、 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65%的产率得到3-[4-(2-Acetylaminoethyl)-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