1-methylaminomethyl-2-naphthol hydrochloride | 5487-67-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-methylaminomethyl-2-naphthol hydrochloride
• 英文别名: 1-Methylaminomethyl-naphthol-(2)；1-[(Methylamino)methyl]naphthalen-2-ol hydrochloride；1-(methylaminomethyl)naphthalen-2-ol;hydrochloride
• CAS: 5487-67-2
• 化学式: C₁₂H₁₃NO*ClH
• 分子量: 223.702
• InChiKey: KHHPKBJJSDGMQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  32.3
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methylaminomethyl-2-naphthol hydrochloride 在 C.I.酸性橙108 作用下， 生成 1-[[(2-羟基萘-1-基)甲基-甲基-氨基]甲基]萘-2-醇
  参考文献：
  名称：

  Synthesis and Study of Mannich Bases from 2-Naphthol and Primary Amines¹

  摘要：

  DOI：

  10.1021/jo01025a038
• 作为产物：
  描述：

  2-甲基-1,3-二氢苯并[f][1,3]苯并恶嗪 在 盐酸 作用下， 以 丙醇 为溶剂， 反应 0.5h， 以91%的产率得到1-methylaminomethyl-2-naphthol hydrochloride
  参考文献：
  名称：

  Synthesis and cardiovascular evaluation of N-substituted 1-aminomethyl-2-naphthols

  摘要：

  A series of 1-alkylaminomethylnaphthols have been prepared. These compounds were readily prepared in good yields by addition of 2-naphthol to formalin and alkylamines. The hypotensive and bradycardiac effects of these compounds in normotensive rats as well as their in vitro inotropic and aortic contraction effects in isolated rat left atria and aorta have been evaluated. A higher depressor and bradycardiac activity was found for compounds substituted on nitrogen by naphthol with primary amines, i.e., ethylamine, propylamine, isopropylamine, or butylamine and with a cyclic secondary amine, i.e., pyrrolidinyl. These compounds produced biphasic changes in contractile force in isolated rat atria which was correlated to blood pressure and heart rate activity. 1-Isopropylaminomethyl-2-naphthol hydrochloride relaxed isolated rat aortic rings precontracted with high extracellular K+ (80 mM) and Ca2+ (1.9 mM). The suppressive effects of the compounds may involve a direct inhibition of Ca2+ channels. The biological activity of these compounds can be explained in terms of substitution on nitrogen. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(99)00204-4

文献信息

• Synthesis and Study of Mannich Bases from 2-Naphthol and Primary Amines¹
  作者：William J. Burke、Wilmonte A. Nasutavicus、Carl Weatherbee

  DOI：10.1021/jo01025a038

  日期：1964.2
• Synthesis and cardiovascular evaluation of N-substituted 1-aminomethyl-2-naphthols
  作者：A Shen

  DOI：10.1016/s0223-5234(99)00204-4

  日期：1999.10

  A series of 1-alkylaminomethylnaphthols have been prepared. These compounds were readily prepared in good yields by addition of 2-naphthol to formalin and alkylamines. The hypotensive and bradycardiac effects of these compounds in normotensive rats as well as their in vitro inotropic and aortic contraction effects in isolated rat left atria and aorta have been evaluated. A higher depressor and bradycardiac activity was found for compounds substituted on nitrogen by naphthol with primary amines, i.e., ethylamine, propylamine, isopropylamine, or butylamine and with a cyclic secondary amine, i.e., pyrrolidinyl. These compounds produced biphasic changes in contractile force in isolated rat atria which was correlated to blood pressure and heart rate activity. 1-Isopropylaminomethyl-2-naphthol hydrochloride relaxed isolated rat aortic rings precontracted with high extracellular K+ (80 mM) and Ca2+ (1.9 mM). The suppressive effects of the compounds may involve a direct inhibition of Ca2+ channels. The biological activity of these compounds can be explained in terms of substitution on nitrogen. (C) 1999 Editions scientifiques et medicales Elsevier SAS.