((1S,2S)-5-甲氧基-1-甲基-1,2,3,4-四氢-萘-2-基)-二丙胺 | 106499-61-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: ((1S,2S)-5-甲氧基-1-甲基-1,2,3,4-四氢-萘-2-基)-二丙胺
• 英文名称: (1S,2S)-5-methoxy-1-methyl-N,N-dipropyl-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS: 106499-61-0
• 化学式: C₁₈H₂₉NO
• 分子量: 275.434
• InChiKey: BTOJYCTUJJHANF-YOEHRIQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 3.5h， 生成 ((1S,2S)-5-甲氧基-1-甲基-1,2,3,4-四氢-萘-2-基)-二丙胺
  参考文献：
  名称：

  C1-Methylated 5-hydroxy-2-(dipropylamino)tetralins: central dopamine-receptor stimulating activity

  摘要：

  C1-Methylated derivatives of the potent dopaminergic agonist 5-hydroxy-2-(di-n-propylamino)tetralin (6) have been synthesized and tested for central dopamine (DA) receptor stimulating activity, by using biochemical and behavioral tests in rats. Both cis- and trans-5-hydroxy-1-methyl-2-(di-n-propylamino) tetralin (4 and 3) may be classified as central DA-receptor agonists, albeit of lower potency than 6. The results obtained indicate that both 4 and 3 display DA-autoreceptor stimulation capacity. However, only one of the isomers, trans-3, is able to elicit clear-cut postsynaptic DA receptor agonist actions at larger doses. 5-Hydroxy-1,1-dimethyl-2-(n-propylamino) tetralin (5) was found to be inactive.

  DOI：

  10.1021/jm00374a012

文献信息

• Resolved cis- and trans-2-amino-5-methoxy-1-methyltetralins: central dopamine receptor agonists and antagonists
  作者：Anette M. Johansson、Lars Erik Arvidsson、Uli Hacksell、J. Lars G. Nilsson、Kjell Svensson、Arvid Carlsson

  DOI：10.1021/jm00387a004

  日期：1987.4

  A series of 35 stereochemically well-defined C1-methyl-substituted derivatives of the potent dopamine (DA) receptor agonist 5-hydroxy-2-(di-n-propylamino)tetralin (5-OH-DPAT) have been synthesized. The compounds were tested for central DA receptor agonistic and antagonistic activity, by use of biochemical and behavioral tests in rats. In addition, the compounds were tested for in vivo interactions with 5,6-dihydroxy-2-(di-n-propylamino)tetralin (DiPr-5,6-ADTN). On the basis of pharmacological activity profiles, the active compounds have been classified into four groups: classical pre- and postsynaptic DA receptor agonists, DA receptor agonists with preferential action at presynaptic receptors, pre- and postsynaptic DA receptor antagonists, and DA receptor antagonists with preferential action at presynaptic receptors. Results obtained indicate that both 2R and 2S enantiomers of C5-oxygenated 2-aminotetralins may be able to bind to DA receptors but that only 2S antipodes are able to activate the receptors. O-Methylation of the C5-oxygenated (1S,2R)-2-amino-1-methyltetralin derivatives tends to increase their DA receptor antagonistic activity, whereas decrease of the size of the N-substituent(s) from n-propyl to ethyl or methyl appears to increase their activity at postsynaptic DA receptors.
• C1-Methylated 5-hydroxy-2-(dipropylamino)tetralins: central dopamine-receptor stimulating activity
  作者：Uli Hacksell、Anette M. Johansson、Lars Erik Arvidsson、J. Lars G. Nilsson、Stephan Hjorth、Arvid Carlsson、Hakan Wikstroem、Domingo Sanchez、Per Lindberg

  DOI：10.1021/jm00374a012

  日期：1984.8

  C1-Methylated derivatives of the potent dopaminergic agonist 5-hydroxy-2-(di-n-propylamino)tetralin (6) have been synthesized and tested for central dopamine (DA) receptor stimulating activity, by using biochemical and behavioral tests in rats. Both cis- and trans-5-hydroxy-1-methyl-2-(di-n-propylamino) tetralin (4 and 3) may be classified as central DA-receptor agonists, albeit of lower potency than 6. The results obtained indicate that both 4 and 3 display DA-autoreceptor stimulation capacity. However, only one of the isomers, trans-3, is able to elicit clear-cut postsynaptic DA receptor agonist actions at larger doses. 5-Hydroxy-1,1-dimethyl-2-(n-propylamino) tetralin (5) was found to be inactive.