1-amino-N-ethyl-N-n-butyl-3-(1-naphthyl)propan-3-one hydrochloride | 118868-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-amino-N-ethyl-N-n-butyl-3-(1-naphthyl)propan-3-one hydrochloride
• 英文别名: 3-[butyl(ethyl)amino]-1-naphthalen-1-ylpropan-1-one;hydrochloride
• CAS: 118868-68-1
• 化学式: C₁₉H₂₅NO*ClH
• 分子量: 319.875
• InChiKey: UJYNKVFSLGDXAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-amino-N-ethyl-N-n-butyl-3-(1-naphthyl)propan-3-one hydrochloride 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 N-ethyl-N-n-butyl-3-(1-naphthyl)propanamine hydrogen oxalate
  参考文献：
  名称：

  Design and synthesis of propranolol analogs as serotonergic agents

  摘要：

  Serotonin (5-HT) binds with nearly identical affinity at the various central 5-HT binding sites. Few agents bind with selectivity for 5-HT1A sites. The beta-adrenergic antagonist propranolol binds stereoselectively both at 5-HT1A and 5-HT1B sites (with a several-fold selectivity for the latter) and, whereas it is a 5-HT1A antagonist, it appears to be a 5-HT1B agonist. As such, it could serve as a lead compound for the development of new 5-HT1A and 5-HT1B agents. The purpose of the present study was to modify the structure of propranolol in such a manner so as to reduce its affinity for 5-HT1B and beta-adrenergic sites while, at the same time, retaining its affinity for 5-HT1A sites. Removal of the side-chain hydroxyl group of propranolol, and conversion of its secondary amine to a tertiary amine, reduced affinity for 5-HT1B and beta-adrenergic sites. In addition, shortening the side chain by one carbon atom resulted in compounds with affinity for hippocampal 5-HT1A sites comparable to that of racemic propranolol, but with a 30- to 500-fold lower affinity for 5-HT1B sites and a greater than 1000-fold lower affinity for beta-adrenergic sites. The results of these preliminary studies attest to the utility of this approach for the development of novel serotonergic agents.

  DOI：

  10.1021/jm00124a021
• 作为产物：
  描述：

  1-萘乙酮 、 N-乙基正丁胺 以63%的产率得到
  参考文献：
  名称：

  PIERSON, M. EDWARD;LYON, ROBERT A.;TITELER, MILT;KOWALSKI, PAUL;GLENNON, +, J. MED. CHEM., 32,(1989) N, C. 859-863

  摘要：

  DOI：