[4-[(7S)-7-(dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]phenyl] trifluoromethanesulfonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: [4-[(7S)-7-(dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]phenyl] trifluoromethanesulfonate
• 化学式: C₂₃H₂₈F₃NO₃S
• 分子量: 455.541
• InChiKey: RPEWABBGPJLYLS-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 四甲基锡 、 [4-[(7S)-7-(dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]phenyl] trifluoromethanesulfonate 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 molecular sieve 、 2,6-二叔丁基-4-甲基苯酚 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-[4-[(7S)-7-(dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]phenyl]ethanone
  参考文献：
  名称：

  C8-Substituted derivatives of 2-(dipropylamino)tetralin: exploration of the effect of C8-aryl and heteroaryl substituents on the interaction with 5-HT1A-receptor

  摘要：

  In order to further explore the structure-activity relationships of serotonergic 2-aminotetralin derivatives, a total of 12 aryl and heteroaryl substituents have been introduced in the C8-position of 2-(dipropylamino)tetralin. The affinity of the compounds was studied by competition experiments with [H-3]-8-OH-DPAT in rat-brain tissue. In addition, the effects of the compounds were assessed in vivo using biochemical and behavioral tests in rats. Although all the novel derivatives had fairly high affinities for the 5-HT1A receptors, several compounds failed to produce biochemical or behavioral effects indicative of 5-HT1A-receptor stimulation. In addition, they did not appear to be 5-HT1A-receptor antagonists. Hence, the apparent inactivity in vivo may be due to pharmacokinetic factors such as extensive metabolism or poor ability to pass the blood-brain barrier. However, a few compounds in the present series, such as (S)-8-(2-furyl)-2-(dipropylamino)tetralin did produce most of the in vivo pharmacological actions typical of 5-HT1A receptor agonists.

  DOI：

  10.1016/0223-5234(96)88236-5
• 作为产物：
  描述：

  三氟甲磺酸酐 、 4-((S)-7-Dipropylamino-5,6,7,8-tetrahydro-naphthalen-1-yl)-phenol 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 [4-[(7S)-7-(dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]phenyl] trifluoromethanesulfonate
  参考文献：
  名称：

  C8-Substituted derivatives of 2-(dipropylamino)tetralin: exploration of the effect of C8-aryl and heteroaryl substituents on the interaction with 5-HT1A-receptor

  摘要：

  In order to further explore the structure-activity relationships of serotonergic 2-aminotetralin derivatives, a total of 12 aryl and heteroaryl substituents have been introduced in the C8-position of 2-(dipropylamino)tetralin. The affinity of the compounds was studied by competition experiments with [H-3]-8-OH-DPAT in rat-brain tissue. In addition, the effects of the compounds were assessed in vivo using biochemical and behavioral tests in rats. Although all the novel derivatives had fairly high affinities for the 5-HT1A receptors, several compounds failed to produce biochemical or behavioral effects indicative of 5-HT1A-receptor stimulation. In addition, they did not appear to be 5-HT1A-receptor antagonists. Hence, the apparent inactivity in vivo may be due to pharmacokinetic factors such as extensive metabolism or poor ability to pass the blood-brain barrier. However, a few compounds in the present series, such as (S)-8-(2-furyl)-2-(dipropylamino)tetralin did produce most of the in vivo pharmacological actions typical of 5-HT1A receptor agonists.

  DOI：

  10.1016/0223-5234(96)88236-5

文献信息

• C8-Substituted derivatives of 2-(dipropylamino)tetralin: exploration of the effect of C8-aryl and heteroaryl substituents on the interaction with 5-HT1A-receptor
  作者：Y Liu、L Cortizo、H Yu、BE Svensson、T Lewander、U Hacksell

  DOI：10.1016/0223-5234(96)88236-5

  日期：1995.1

  In order to further explore the structure-activity relationships of serotonergic 2-aminotetralin derivatives, a total of 12 aryl and heteroaryl substituents have been introduced in the C8-position of 2-(dipropylamino)tetralin. The affinity of the compounds was studied by competition experiments with [H-3]-8-OH-DPAT in rat-brain tissue. In addition, the effects of the compounds were assessed in vivo using biochemical and behavioral tests in rats. Although all the novel derivatives had fairly high affinities for the 5-HT1A receptors, several compounds failed to produce biochemical or behavioral effects indicative of 5-HT1A-receptor stimulation. In addition, they did not appear to be 5-HT1A-receptor antagonists. Hence, the apparent inactivity in vivo may be due to pharmacokinetic factors such as extensive metabolism or poor ability to pass the blood-brain barrier. However, a few compounds in the present series, such as (S)-8-(2-furyl)-2-(dipropylamino)tetralin did produce most of the in vivo pharmacological actions typical of 5-HT1A receptor agonists.