2-(2-methoxy-5-methylphenyl)ethylamine hydrochloride | 18149-09-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-methoxy-5-methylphenyl)ethylamine hydrochloride
• 英文别名: 2-methoxy-5-methyl-phenethylamine; hydrochloride；2-Methoxy-5-methyl-phenaethylamin; Hydrochlorid；2-(2-Methoxy-5-methylphenyl)ethan-1-amine Hydrochloride；2-(2-methoxy-5-methylphenyl)ethanamine;hydrochloride
• CAS: 18149-09-2
• 化学式: C₁₀H₁₅NO*ClH
• 分子量: 201.696
• InChiKey: VSGMGWMOEOFMRZ-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  2-(2-methoxy-5-methylphenyl)ethylamine hydrochloride 、 乙酸酐 在 sodium acetate 作用下， 以 水 为溶剂， 反应 0.5h， 以79%的产率得到N-<2-(2-methoxy-5-methylphenyl)ethyl>acetamide
  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