8-methoxy-2-phenylacetamido-tetralin | 134865-80-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 8-methoxy-2-phenylacetamido-tetralin
• 英文别名: N-(8-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-2-phenylacetamide
• CAS: 134865-80-8
• 化学式: C₁₉H₂₁NO₂
• 分子量: 295.381
• InChiKey: NBVVSVOKQAVJOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-methoxy-2-phenylacetamido-tetralin 生成 N-((R)-8-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-2-phenyl-acetamide 、 N-((S)-8-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-2-phenyl-acetamide
  参考文献：
  名称：

  Selditz; Copinga; Grol, Pharmazie, 1999, vol. 54, # 3, p. 183 - 191

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-8-甲氧基-1,2,3,4-四氢萘盐酸盐 、 苯乙酰氯 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以61%的产率得到8-methoxy-2-phenylacetamido-tetralin
  参考文献：
  名称：

  2-Amido-8-methoxytetralins: A series of nonindolic melatonin-like agents

  摘要：

  A series of unsubstituted and methoxy-substituted 2-amidotetralins (4a-q) was prepared and evaluated for their ability to compete for 2-[I-125]iodomelatonin binding to chicken retinal membranes and for their potency to inhibit the calcium-dependent release of [H-3]dopamine from rabbit retina. The lead compound, 2-acetamido-8-methoxytetralin (4j), showed a moderate affinity (K(i) = 46 nM) and potency (IC50 = 1.4 nM) at the melatonin receptor. The structural requirements necessary for optimal agonistic activity at the melatonin receptor are as follows. First, the amido group, which should have a small, nonbranched alkyl group, is essential for affinity, and second, the methoxy substituent at the 8-position of the 2-amidotetralin ring is essential for optimal agonistic activity at the melatonin receptor. We concluded that this series of unsubstituted and methoxy-substituted 2-amidotetralins constitutes a class of nonindolic melatonin-like agents that can be used as pharmacological tools to further characterize melatonin receptors and to elucidate the mode of action of melatonin.

  DOI：

  10.1021/jm00072a008