5-amino-2-(N-n-propyl-N-propionylamino)-1,2,3,4-tetrahydronaphthalene | 81185-12-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5-amino-2-(N-n-propyl-N-propionylamino)-1,2,3,4-tetrahydronaphthalene
• 英文别名: 5-Amino-2-(N-propionyl-N-n-propyl-amino)-tetraline；N-(5-amino-1,2,3,4-tetrahydronaphthalen-2-yl)-N-propylpropanamide
• CAS: 81185-12-8
• 化学式: C₁₆H₂₄N₂O
• 分子量: 260.379
• InChiKey: JBQSYNPWPVWVDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-amino-2-(N-n-propyl-N-propionylamino)-1,2,3,4-tetrahydronaphthalene 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以90%的产率得到5-amino-2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  5-, 6-, 7- and 8-amino-2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalenes: centrally acting DA and 5-HT1A agonists

  摘要：

  5-, 6-, 7- and 8-Amino-2-(NN-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene were synthesized and compared with the corresponding phenolic compounds in vivo and in vitro for their effects on central serotonergic (5-HT1A) and dopaminergic (D2) systems. The 5- and 8-amino isomers surprisingly showed a 100-fold lower affinity for D2 and 5-HT1A receptors, respectively, than their corresponding phenols. This was also reflected in vivo. The 6-amino- and hydroxy-isomers were equipotent, while the 7-amino compound showed in vivo effects both on dopaminergic and serotonergic systems, the latter not being noticed in vitro. Intermediates 8-bromo-2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene and 2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene-8-carboxylic acid methyl ester were also tested and found to be quite potent 5-HT1A agonists.

  DOI：

  10.1016/0223-5234(93)90028-d
• 作为产物：
  描述：

  8-chloro-2-(n-propylamino)-1,2,3,4-tetrahydronaphthalene 在 palladium on activated charcoal 硫酸 、 硝酸 、 ammonium formate 、 三乙胺 作用下， 以 硝基甲烷 、 乙醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 5-amino-2-(N-n-propyl-N-propionylamino)-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  5-, 6-, 7- and 8-amino-2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalenes: centrally acting DA and 5-HT1A agonists

  摘要：

  5-, 6-, 7- and 8-Amino-2-(NN-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene were synthesized and compared with the corresponding phenolic compounds in vivo and in vitro for their effects on central serotonergic (5-HT1A) and dopaminergic (D2) systems. The 5- and 8-amino isomers surprisingly showed a 100-fold lower affinity for D2 and 5-HT1A receptors, respectively, than their corresponding phenols. This was also reflected in vivo. The 6-amino- and hydroxy-isomers were equipotent, while the 7-amino compound showed in vivo effects both on dopaminergic and serotonergic systems, the latter not being noticed in vitro. Intermediates 8-bromo-2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene and 2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene-8-carboxylic acid methyl ester were also tested and found to be quite potent 5-HT1A agonists.

  DOI：

  10.1016/0223-5234(93)90028-d

文献信息

• Method of treating disorders of the dopaminergic systems using
  申请人：Boehringer Ingelheim KG

  公开号：US05196454A1

  公开（公告）日：1993-03-23

  The invention relates to novel 2,5-diaminotetralines of the formula: ##STR1## wherein R1, R2, R3 and R4 are defined herein, processes for preparing them and their use in pharmaceutical compositions. The novel 2,5-diaminotetralines are useful in treating diseases caused by disorders of the dopaminergic systems.

  这项发明涉及公式为：##STR1##的新型2,5-二氨基四氢萘，其中R1、R2、R3和R4在此处定义，以及用于制备它们的方法和它们在制药组合物中的用途。这种新型2,5-二氨基四氢萘在治疗由多巴胺系统紊乱引起的疾病中很有用。
• Neue 2,5-Diaminotetraline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
  申请人：BOEHRINGER INGELHEIM KG

  公开号：EP0402923A2

  公开（公告）日：1990-12-19

  Die Erfindung betrifft neue 2,5-Diaminotetraline, Verfahren zur ihrer Herstellung und ihre Verwendung als Arzneimittel.

  本发明涉及新的 2,5-二氨基四氢萘，其制备工艺及其作为药物的用途。
• US5196454A
  申请人：——

  公开号：US5196454A

  公开（公告）日：1993-03-23
• 5-, 6-, 7- and 8-amino-2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalenes: centrally acting DA and 5-HT1A agonists
  作者：P Stjernlöf、T Elebring、B Andersson、A Svensson、K Svensson、A Ekman、A Carlsson、H Wikström

  DOI：10.1016/0223-5234(93)90028-d

  日期：1993.1

  5-, 6-, 7- and 8-Amino-2-(NN-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene were synthesized and compared with the corresponding phenolic compounds in vivo and in vitro for their effects on central serotonergic (5-HT1A) and dopaminergic (D2) systems. The 5- and 8-amino isomers surprisingly showed a 100-fold lower affinity for D2 and 5-HT1A receptors, respectively, than their corresponding phenols. This was also reflected in vivo. The 6-amino- and hydroxy-isomers were equipotent, while the 7-amino compound showed in vivo effects both on dopaminergic and serotonergic systems, the latter not being noticed in vitro. Intermediates 8-bromo-2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene and 2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene-8-carboxylic acid methyl ester were also tested and found to be quite potent 5-HT1A agonists.