8-bromo-2-di-n-propylamino-1,2,3,4-tetrahydronaphthalene | 117347-13-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 8-bromo-2-di-n-propylamino-1,2,3,4-tetrahydronaphthalene
• 英文别名: 8-bromo-2-(di-n-propylamino)tetralin；2-Di-n-propylamino-8-bromo1,2,3,4-tetrahydronaphthalene；8-Bromo-2-N,N-di-n-propylaminotetralin；2-dipropylamino-8-bromo-1,2,3,4-tetrahydronaphthalene；8-Bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthalene；8-bromo-N,N-dipropyl-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS: 117347-13-4
• 化学式: C₁₆H₂₄BrN
• 分子量: 310.277
• InChiKey: MRVOVSJOIOFTKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-bromo-2-di-n-propylamino-1,2,3,4-tetrahydronaphthalene 在 正丁基锂 、 草酸氯化物 、 二环己胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 (+/-)-methyl 2-(dipropylamino)tetralin-8-carboxylate
  参考文献：
  名称：

  Novel [(diazomethyl)carbonyl]-1,2,3,4-tetrahydronaphthalene derivatives as potential photoaffinity ligands for the 5-HT1A receptor

  摘要：

  The photolabile (diazomethyl)carbonyl function was introduced into the 8-position of 2-(N,N-di-n-propyl-amino)-1,2,3,4-tetrahydronaphthalene in three ways, resulting in the ether 8-[[(diazomethyl)carbonyl]methoxy]-2-(N,N-di-n-propylamino)-1,2,3,4- tetrahydronaphthalene (2), the ester 8-(diazoacetoxy)-2-(N,N-di-n-propyl-amino)-1,2,3,4- tetrahydronaphthalene (3), and the ketone 8-[(diazomethyl)carbonyl]-2-(N,N-di-n-propylamino)- 1,2,3,4-tetrahydronaphthalene (4). Specific binding of these compounds at the 5-hydroxytryptamine1A sites in rat brain membranes labeled with 1 nM [3H]-8-hydroxy-2-(N,N-di-n-propylamino)- 1,2,3,4-tetrahydronaphthalene (8-OH-DPAT) showed IC50 values of ca. 75, 125, and 25 nM, respectively, for the three compounds. Photolysis of methanolic solutions of 2-4 in the absence of receptor proteins lead in each case to an abundance of Wolff-rearranged products. In the case of ether 2, subsequent beta-elimination to 8-OH-DPAT removed this compound from serious consideration as a photoaffinity ligand. Ester 3 and ketone 4 were photolysed in vitro. Whereas ester 3 was ineffective in decreasing the specific binding of [3H]-8-OH-DPAT, ketone 4 decreased 40% of the specific binding of [3H]-8-OH-DPAT in the presence (but not the absence) of ultraviolet light. Thus this ketone emerges from these studies as a good candidate for a photoaffinity label for the 5-hydroxytrypatamine1A receptor.

  DOI：

  10.1021/jm00165a011
• 作为产物：
  描述：

  2-溴苯乙酰氯 在 三氯化铝 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 53.0h， 生成 8-bromo-2-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
• 作为试剂：
  描述：

  (8-Bromo-3,4-dihydro-naphthalen-2-yl)-dipropyl-amine 、 氰基硼氢化钠 、 盐酸 、 sodium hydroxide 在 乙醚 、 水 、 氯化钠 、 Sodium sulfate-III 、 8-bromo-2-di-n-propylamino-1,2,3,4-tetrahydronaphthalene 、 alumina 、 二氯甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以gave the product as a light yellow oil (7.8 gm, 57%)的产率得到8-bromo-2-di-n-propylamino-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Method of inhibiting gastric acid secretion

  摘要：

  本发明提供了一种通过给哺乳动物注射5-HT1A激动剂化合物或其药学上可接受的盐来抑制胃酸分泌的方法。

  公开号：

  US05096908A1

文献信息

• 8-Substituted 2-aminotetralins
  申请人：Bayer Aktiengesellschaft

  公开号：US04873262A1

  公开（公告）日：1989-10-10

  New 8-substituted 2-aminotetralins can be prepared from the corresponding aminotetralins or tetralones. They can be used in medicaments.

  新的8-取代的2-氨基四氢萘可以从相应的氨基四氢萘或四氢萘酮制备而成。它们可以用于药物。
• Method of inhibiting gastric acid secretion with benzodioxanes
  申请人：Eli Lilly and Company

  公开号：US05158956A1

  公开（公告）日：1992-10-27

  The present invention provides a method of inhibiting gastric acid secretion in mammals by administering a 5-HT1A agonist compound or a pharmaceutically acceptable salt thereof.

  本发明提供了一种通过给哺乳动物施用5-HT1A激动剂化合物或其药用盐来抑制胃酸分泌的方法。
• Ring-substituted 2-amino-1,2,3,4-tetra-hydronaphthalenes
  申请人：Eli Lilly and Company

  公开号：US05389687A1

  公开（公告）日：1995-02-14

  The present invention provides novel ring-substituted 2-amino-1,2,3,4-tetrahydronaphthalenes which exhibit binding activity at the serotonin 1A receptor.

  本发明提供了一种新型的环替代的2-氨基-1,2,3,4-四氢萘烯衍生物，其在5-羟色胺1A受体上表现出结合活性。
• Therapeutically useful 2-aminotetralin derivatives
  申请人：The Upjohn Company

  公开号：US06331636B1

  公开（公告）日：2001-12-18

  This invention is therapeutically useful 2-aminotetralins and pharmaceutically acceptable acid addition salts thereof of the formula These compounds are useful to treat central nervous system disorders, hypertension, diabetes, sexual impotency and to control appetite.

  这项发明是治疗有用的2-氨基四氢萘及其药用可接受的酸盐，其化学式为。这些化合物可用于治疗中枢神经系统疾病、高血压、糖尿病、性功能障碍以及控制食欲。
• Ring-substituted 2-amino-1,2,3,4-tetra-hydronaphthalenes and
  申请人：Eli Lilly and Company

  公开号：US05286753A1

  公开（公告）日：1994-02-15

  The present invention provides novel ring-substituted 2-amino-1,2,3,4-tetrahydronaphthalenes, 3-aminochromanes, and 3-aminothiochromanes, including their corresponding sulfoxides and sulfones, which ring-substituted compounds exhibit agonist activity at the serotonin 1A receptor.

  本发明提供了新型的环取代2-氨基-1,2,3,4-四氢萘烯、3-氨基色酮和3-氨基硫色酮，包括它们对应的亚氧化物和砜化物，这些环取代化合物在5-羟色胺1A受体上表现出激动剂活性。