1-(aminomethyl)-6,7-dimethoxytetralin | 85221-59-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-(aminomethyl)-6,7-dimethoxytetralin
• 英文别名: (6,7-Dimethoxy-1,2,3,4-tetrahydronaphthalen-1-yl)methanamine；(6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-1-yl)methanamine
• CAS: 85221-59-6
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: XRRAMPRLMQTVDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(aminomethyl)-6,7-dimethoxytetralin 在 platinum(IV) oxide 、 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 生成 1-<(methyl-2-propylamino)methyl>-6,7-dimethoxytetralin
  参考文献：
  名称：

  1-(Aminomethyl)-6,7-dihydroxytetralin derivatives: synthesis and assessment of dopamine-like effects

  摘要：

  The title compounds were designed as flexible congeners of trans-octahydrobenz[h]isoquinoline, in which the dopamine moiety can exist in the alpha conformation. Extremely low dopamine-like effects in the title series in the cat cardioaccelerator nerve assay paralleled low activity in the trans-octahydrobenz[h]isoquinoline compounds and was consistent with a prior proposal of the presence of a bulky region on the dopamine receptor(s).

  DOI：

  10.1021/jm00360a006

文献信息

• Novel Sulphamides and Sulphonamides Incorporating the Tetralin Scaffold as Carbonic Anhydrase and Acetylcholine Esterase Inhibitors
  作者：Akın Akıncıoğlu、Meryem Topal、İlhami Gülçin、Süleyman Göksu

  DOI：10.1002/ardp.201300273

  日期：2014.1

  amino, aminomethyl tetralins and benzyl alcohol with chlorosulphonyl isocyanate (CSI) afforded sulphamoyl carbamates. The sulphamoyl carbamates were converted to sulphamides by palladium‐catalysed hydrogenolysis. Sulphonamides were synthesized from the reactions of amines with MeSO2Cl. Inhibition of human (h) carbonic anhydrase (CA) isoenzymes (hCA I, hCA II) and acetylcholine esterase (AChE) was investigated

  氨基、氨甲基四氢萘和苯甲醇与氯磺酰基异氰酸酯 (CSI) 反应得到氨磺酰氨基甲酸酯。氨磺酰氨基甲酸酯通过钯催化的氢解转化为磺酰胺。磺胺是由胺与 MeSO2Cl 反应合成的。用合成的化合物研究了人 (h) 碳酸酐酶 (CA) 同工酶 (hCA I、hCA II) 和乙酰胆碱酯酶 (AChE) 的抑制作用。hCA I 和 hCA II 在低微摩尔或亚微摩尔范围内受到抑制。Ki 值对 hCA I 的范围为 0.91–9.56 µM，对 hCA II 的范围为 3.70–27.88 µM。磺胺类药物 11-13 和磺胺类药物 14-16 对 AChE 具有中等抑制能力。这些发现表明新型磺酰胺 11-13 和磺酰胺 14-16 作为 AChE 和 CA 同工酶抑制剂。
• 1-(Aminomethyl)-6,7-dihydroxytetralin derivatives: synthesis and assessment of dopamine-like effects
  作者：Joseph G. Cannon、Zurilma Perez、John Paul Long、Mustafa Ilhan

  DOI：10.1021/jm00360a006

  日期：1983.6

  The title compounds were designed as flexible congeners of trans-octahydrobenz[h]isoquinoline, in which the dopamine moiety can exist in the alpha conformation. Extremely low dopamine-like effects in the title series in the cat cardioaccelerator nerve assay paralleled low activity in the trans-octahydrobenz[h]isoquinoline compounds and was consistent with a prior proposal of the presence of a bulky region on the dopamine receptor(s).