(1S,2S)-(-)-trans-7-methoxy-2-n-propylamino-1-tetralol | 131103-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1S,2S)-(-)-trans-7-methoxy-2-n-propylamino-1-tetralol
• 英文别名: (1S,2S)-7-methoxy-2-(propylamino)-1,2,3,4-tetrahydronaphthalen-1-ol
• CAS: 131103-72-5
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: DEKFVABYOMDBAL-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S)-(-)-trans-7-methoxy-2-n-propylamino-1-tetralol 生成 trans-9-methoxy-4-n-propyl-2,3,4a,5,6,10b-hexahydro-4H-naphtho<1,2-b><1,4>thiazine hydrochloride
  参考文献：
  名称：

  PERRONE, ROBERTO;BERARDI, FRANCESCO;TORTORELLA, VINCENZO;RACAGNI, GIORGIO+, FARMACO, 45,(1990) N, C. 479-488

  摘要：

  DOI：
• 作为产物：
  描述：

  7-甲氧基-1-萘满酮 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 氢气 、 N,N'-二环己基碳二亚胺 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 甲醚 、 水 、 乙二醇 、 正丁醇 为溶剂， 反应 6.0h， 生成 (1S,2S)-(-)-trans-7-methoxy-2-n-propylamino-1-tetralol
  参考文献：
  名称：

  Synthesis of 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, a new class of dopamine agonists

  摘要：

  A series of tricyclic oxazines, namely, the 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, have been synthesized and assayed for dopamine agonist activity. One of the members of this series, compound (+)VII-15, was found to be a remarkably potent agonist in vivo when tested in the standard 6-hydroxydopamine lesioned rat assay. The absolute configuration of the compound corresponds to that found in the active isomer of apomorphine. Its activity at the alpha 2 receptor (vs. [3H]clonidine) is relatively low. It also failed to stimulate the synthesis of cAMP in the carp retina assay, thus giving the compound a highly selective profile in favor of the D2 receptor.

  DOI：

  10.1021/jm00378a014

文献信息

• Hexahydronaphth(1,2-b)-1,4-oxazines, process for their preparation and pharmaceutical formulation containing them
  申请人：Merck & Co., Inc.

  公开号：EP0080115A2

  公开（公告）日：1983-06-01

  Hexahydronaphth[1,2-b]-1,4-oxazines have dopaminergic activity and display α2-adrenergic receptor antagonism. They are useful in the treatment of parkinsonism, depression and hypertension. An important method of preparation is by ring closure of the appropriate 2-chloroacetamido- tetrahydronaphthalen-1-ol and reduction of the resulting cyclic amide carbonyl group.

  六氢萘并[1,2-b]-1,4-噁嗪具有多巴胺能活性，并显示出α2-肾上腺素能受体拮抗作用。 它们可用于治疗帕金森病、抑郁症和高血压。 一种重要的制备方法是将适当的 2-氯乙酰胺基四氢萘-1-醇闭环，并还原由此产生的环状酰胺羰基。
• Further Characterization of Structural Requirements for Ligands at the Dopamine D₂ and D₃ Receptor:  Exploring the Thiophene Moiety
  作者：Durk Dijkstra、Nienke Rodenhuis、Erik S. Vermeulen、Thomas A. Pugsley、Lawrence D. Wise、Håkan V. Wikström

  DOI：10.1021/jm001015a

  日期：2002.7.1

  The present study describes the synthesis and in vitro pharmacology of a novel series of dopaminergic agents in which the classical phenylethylamine pharmacophore is replaced by a thienylethylamine moiety. In general, the novel compounds showed a moderate affinity for the dopamine (DA) D-2 and D-3 receptors. When the thienylethylamine moiety is fixed in a rigid system, the affinity for the DA receptor is significantly increased. However, in the tricyclic hexahydrothianaphthoxazine structure, the affinity for the DA receptors is diminished.
• Perrone; Berardi; Tortorella, Il Farmaco, 1990, vol. 45, # 5, p. 479 - 488
  作者：Perrone、Berardi、Tortorella、Racagni、Rovescalli

  DOI：——

  日期：——
• PERRONE, ROBERTO;BERARDI, FRANCESCO;TORTORELLA, VINCENZO;RACAGNI, GIORGIO+, FARMACO, 45,(1990) N, C. 479-488
  作者：PERRONE, ROBERTO、BERARDI, FRANCESCO、TORTORELLA, VINCENZO、RACAGNI, GIORGIO+

  DOI：——

  日期：——
• Synthesis of 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, a new class of dopamine agonists
  作者：James H. Jones、Paul S. Anderson、John J. Baldwin、Bradley V. Clineschmidt、David E. McClure、George F. Lundell、William C. Randall、Gregory E. Martin、Michael Williams

  DOI：10.1021/jm00378a014

  日期：1984.12

  A series of tricyclic oxazines, namely, the 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, have been synthesized and assayed for dopamine agonist activity. One of the members of this series, compound (+)VII-15, was found to be a remarkably potent agonist in vivo when tested in the standard 6-hydroxydopamine lesioned rat assay. The absolute configuration of the compound corresponds to that found in the active isomer of apomorphine. Its activity at the alpha 2 receptor (vs. [3H]clonidine) is relatively low. It also failed to stimulate the synthesis of cAMP in the carp retina assay, thus giving the compound a highly selective profile in favor of the D2 receptor.