2-((1S,2R)-2-Dipropylamino-cyclopropyl)-phenol | 111001-15-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-((1S,2R)-2-Dipropylamino-cyclopropyl)-phenol
• 英文别名: 2-[(1S,2R)-2-(dipropylamino)cyclopropyl]phenol
• CAS: 111001-15-1
• 化学式: C₁₅H₂₃NO
• 分子量: 233.354
• InChiKey: LARFBOKVMNMLSW-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1R,2S)-2-(2-methoxyphenyl)-N,N-dipropylcyclopropylamine hydrochloride 在 氢溴酸 作用下， 反应 2.0h， 以75%的产率得到2-((1S,2R)-2-Dipropylamino-cyclopropyl)-phenol
  参考文献：
  名称：

  N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: novel central 5-hydroxytryptamine-receptor agonists

  摘要：

  N,N-Dialkylated monophenolic derivatives of trans-2-phenylcyclopropylamine were synthesized and tested for central 5-hydroxytryptamine (5-HT) and dopamine (DA) receptor stimulating activity by use of a biochemical test method in rats. A hydroxy substituent in the 2- or 3-position of the phenyl ring was required for 5-HT-receptor stimulation. N,N-Diethyl or N,N-di-n-propyl substitution gave the most potent 5-HT-receptor agonists. The 4-hydroxy and 3,4-dihydroxy derivatives of trans-2-phenyl-N,N-di-n-propylcyclopropylamine were inactive at central DA and 5-HT receptors. In contrast, the corresponding 3-hydroxy derivative 18 and some of its derivatives weakly affected both DA and NE synthesis. Two of the most potent 5-HT-receptor agonists, trans-2-(2-hydroxyphenyl)-N,N-di-n-propylcyclopropylamine (8) and the 3-hydroxy isomer 18 were resolved into the enantiomers. The 1R,2S enantiomers of 8 and 18 displayed 5-HT activity, while the 1S,2R enantiomers were inactive. Compound (1R,2S)-18, but not (1R,2S)-8, weakly affected rat brain DA and NE synthesis.

  DOI：

  10.1021/jm00396a014

文献信息

• Treatment of anhedonia
  申请人：Nathanson L. Donald

  公开号：US20060217394A1

  公开（公告）日：2006-09-28

  A therapeutic method for the enhancement of mood in patients afflicted with iatrogenic anhedonia secondary to chronic increases in the availability and/or efficiency of serotonin, with or without increases in the availability and/or efficiency of norepinephrine.

  一种治疗方法，用于改善因长期增加血清素的供应量和/或效率，同时或不增加去甲肾上腺素的供应量和/或效率而继发的先天性失神症患者的情绪。
• ARVIDSSON, LARS-ERIK;JOHANSSON, ANETTE M.;HACKSELL, ULI;NILSSON, J. LARS +, J. MED. CHEM., 31,(1988) N 1, 92-99
  作者：ARVIDSSON, LARS-ERIK、JOHANSSON, ANETTE M.、HACKSELL, ULI、NILSSON, J. LARS +

  DOI：——

  日期：——
• N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: novel central 5-hydroxytryptamine-receptor agonists
  作者：Lars Erik Arvidsson、Anette M. Johansson、Uli Hacksell、J. Lars G. Nilsson、Kjell Svensson、Stephan Hjorth、Tor Magnusson、Arvid Carlsson、Per Lindberg

  DOI：10.1021/jm00396a014

  日期：1988.1

  N,N-Dialkylated monophenolic derivatives of trans-2-phenylcyclopropylamine were synthesized and tested for central 5-hydroxytryptamine (5-HT) and dopamine (DA) receptor stimulating activity by use of a biochemical test method in rats. A hydroxy substituent in the 2- or 3-position of the phenyl ring was required for 5-HT-receptor stimulation. N,N-Diethyl or N,N-di-n-propyl substitution gave the most potent 5-HT-receptor agonists. The 4-hydroxy and 3,4-dihydroxy derivatives of trans-2-phenyl-N,N-di-n-propylcyclopropylamine were inactive at central DA and 5-HT receptors. In contrast, the corresponding 3-hydroxy derivative 18 and some of its derivatives weakly affected both DA and NE synthesis. Two of the most potent 5-HT-receptor agonists, trans-2-(2-hydroxyphenyl)-N,N-di-n-propylcyclopropylamine (8) and the 3-hydroxy isomer 18 were resolved into the enantiomers. The 1R,2S enantiomers of 8 and 18 displayed 5-HT activity, while the 1S,2R enantiomers were inactive. Compound (1R,2S)-18, but not (1R,2S)-8, weakly affected rat brain DA and NE synthesis.