1-(2-methoxynaphthyl)-2-aminopropane | 156482-76-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-methoxynaphthyl)-2-aminopropane
• 英文别名: 1-(2-Methoxynaphthalen-1-yl)propan-2-amine
• CAS: 156482-76-7
• 化学式: C₁₄H₁₇NO
• mdl: MFCD08452678
• 分子量: 215.295
• InChiKey: HWTUIQCVASRTMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-methoxynaphthyl)-2-aminopropane 、 三氟乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以34%的产率得到N-<1-methyl-2-(2-methoxynaphthyl)ethyl>trifluoroacetamide
  参考文献：
  名称：

  Design and Synthesis of New Naphthalenic Derivatives as Ligands for 2-[125I]Iodomelatonin Binding Sites

  摘要：

  New melatonin-like agents were designed from the frameworks of 2,5-dimethoxyphenethylamine, an important structural moiety for the 5-HT receptor, and (2-methoxynaphthyl)-ethylamine. The compounds were synthesized by classical methods and evaluated in binding assays with chicken brain membranes using 2-[I-125]iodomelatonin as the radioligand. Preliminary studies on the series of N-acyl-disubstituted phenethylamines showed the favorable role of the methoxy group in the ortho position of the side chain on the affinity for the receptor K-i = 8 +/- 0.2 nM) for N-[2-(2-methoxy-5-bromophenyl)ethyl]propionamide (3o). This effect was confirmed in a series of the naphthalene derivatives, a bioisosteric moiety of the indole ring, and several potent ligands for melatonin binding sites were prepared such as N-[2-(2-methoxynaphthyl)ethyl]propionamide (4b) (K-i = 0.67 +/- 0.05 nM) and N-[2-(2,7-dimethoxynaphthyl)ethyl]cyclopropylformamide (K-i = 0.05 +/- 0.004 nM) (4k). Structure-activity relationships are discussed with regard to melatonin and bioisosteric naphthalenic compound 2. The K-i value for 4b was affected to a similar extent to that of melatonin by GTP-gamma-S or Mn2+ in competition experiments, suggesting an agonist profile for this compound.

  DOI：

  10.1021/jm00012a004
• 作为产物：
  描述：

  2-甲氧基-1-萘醛 在 乙酸铵 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 1-(2-methoxynaphthyl)-2-aminopropane
  参考文献：
  名称：

  Design and Synthesis of New Naphthalenic Derivatives as Ligands for 2-[125I]Iodomelatonin Binding Sites

  摘要：

  New melatonin-like agents were designed from the frameworks of 2,5-dimethoxyphenethylamine, an important structural moiety for the 5-HT receptor, and (2-methoxynaphthyl)-ethylamine. The compounds were synthesized by classical methods and evaluated in binding assays with chicken brain membranes using 2-[I-125]iodomelatonin as the radioligand. Preliminary studies on the series of N-acyl-disubstituted phenethylamines showed the favorable role of the methoxy group in the ortho position of the side chain on the affinity for the receptor K-i = 8 +/- 0.2 nM) for N-[2-(2-methoxy-5-bromophenyl)ethyl]propionamide (3o). This effect was confirmed in a series of the naphthalene derivatives, a bioisosteric moiety of the indole ring, and several potent ligands for melatonin binding sites were prepared such as N-[2-(2-methoxynaphthyl)ethyl]propionamide (4b) (K-i = 0.67 +/- 0.05 nM) and N-[2-(2,7-dimethoxynaphthyl)ethyl]cyclopropylformamide (K-i = 0.05 +/- 0.004 nM) (4k). Structure-activity relationships are discussed with regard to melatonin and bioisosteric naphthalenic compound 2. The K-i value for 4b was affected to a similar extent to that of melatonin by GTP-gamma-S or Mn2+ in competition experiments, suggesting an agonist profile for this compound.

  DOI：

  10.1021/jm00012a004

文献信息

• Arylalkyl(thio)amides ayant une affinité sélective pour les récepteurs de la mélatonine et leur procédé de préparation
  申请人：ADIR ET COMPAGNIE

  公开号：EP0591057B1

  公开（公告）日：1996-07-10
• US5464872A
  申请人：——

  公开号：US5464872A

  公开（公告）日：1995-11-07
• US5554642A
  申请人：——

  公开号：US5554642A

  公开（公告）日：1996-09-10
• US5604261A
  申请人：——

  公开号：US5604261A

  公开（公告）日：1997-02-18
• US5708020A
  申请人：——

  公开号：US5708020A

  公开（公告）日：1998-01-13