(7-甲氧基-3,4-二氢-萘-2-基)-二丙胺 | 1025895-71-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (7-甲氧基-3,4-二氢-萘-2-基)-二丙胺
• 英文名称: (7-Methoxy-3,4-dihydro-naphthalen-2-yl)-dipropyl-amine
• 英文别名: 7-methoxy-N,N-dipropyl-3,4-dihydronaphthalen-2-amine
• CAS: 1025895-71-9
• 化学式: C₁₇H₂₅NO
• 分子量: 259.392
• InChiKey: VFNFBWONFYPDFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (7-甲氧基-3,4-二氢-萘-2-基)-二丙胺 在 吡啶 、 盐酸 、 platinum(IV) oxide 、 盐酸羟胺 、 氨 、 氢溴酸 、 氢气 、 sodium 、 溶剂黄146 、 sodium sulfate 、 异丙醇 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 25.0 ℃ 、202.65 kPa 条件下， 反应 5.5h， 生成 N-<7-(dipropylamino)-5,6,7,8-tetrahydro-2-naphthalenyl>-2-(hydroxyimino)acetamide
  参考文献：
  名称：

  Drug design via pharmacophore identification. Dopaminergic activity of 3H-benz[e]indol-8-amines and their mode of interaction with the dopamine receptor

  摘要：

  The design and synthesis of a series of 3H-benz[e]indol-8-amines are described. Two of the compounds are potent, orally active dopaminergic agents as established by their ability to induce contralateral turning in rats with unilateral 6-hydroxydopamine-induced lesions of the nigrostriatal pathway, to induce ambulation in rats rendered akinetic by bilateral injections of 6-hydroxydopamine into the anterolateral hypothalamus, and to antagonize reserpine-induced catalepsy in mice. The dopamine agonist activity of the 3H-benz[e]indol-8-amines establishes that a pyrrolo ring and a phenolic hydroxyl group can interact similarly with the dopamine receptor and provides evidence for the existence of a hydrogen-bond acceptor nucleus on the dopamine receptor macromolecule that is involved in the behavioral manifestations of dopamine agonists.

  DOI：

  10.1021/jm00155a011
• 作为产物：
  描述：

  7-甲氧基-2-萘满酮 、 二正丙胺 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 144.0h， 生成 (7-甲氧基-3,4-二氢-萘-2-基)-二丙胺
  参考文献：
  名称：

  Phenolic derivatives of 1,2-methano-N,N-dipropyl-1,2,3,4-tetrahydronaphth-2-ylamine. Structural hybrids of 2-aminotetralin- and phenylcyclopropylamine-derived 5-HT1A-receptor agonists

  摘要：

  Three phenolic derivatives of 1,2-methano-N,N-dipropyl- 1,2,3,4-tetrahydronaphth-2-ylamine 6-8 were synthesized as structural hybrids of the potent 5-HT1A-receptor agonist 8-OH-DPAT 1 and 2 related phenolic phenylcyclopropylamines 4 and 5. The new compounds were assayed for 5-HT1A-receptor affinity and efficacy in vitro. Hybrids 6 and 7 were considered to be inactive but 8 had a K(i) value of 130 nM for [H-3]-8-OH-DPAT labelled 5-HT1A-receptors and produced an inhibition of the cAMP-production in the VIP-stimulated adenylyl cyclase assay. Thus, 8 is able to bind to and stimulate 5-HT1A-receptors. The results are discussed in relation to a previously described 3-D model for 5-HT1A-receptor agonists.

  DOI：

  10.1016/0223-5234(93)90126-y

文献信息

• Drug design via pharmacophore identification. Dopaminergic activity of 3H-benz[e]indol-8-amines and their mode of interaction with the dopamine receptor
  作者：Andre A. Asselin、Leslie G. Humber、Katherine Voith、Geoffrey Metcalf

  DOI：10.1021/jm00155a011

  日期：1986.5

  The design and synthesis of a series of 3H-benz[e]indol-8-amines are described. Two of the compounds are potent, orally active dopaminergic agents as established by their ability to induce contralateral turning in rats with unilateral 6-hydroxydopamine-induced lesions of the nigrostriatal pathway, to induce ambulation in rats rendered akinetic by bilateral injections of 6-hydroxydopamine into the anterolateral hypothalamus, and to antagonize reserpine-induced catalepsy in mice. The dopamine agonist activity of the 3H-benz[e]indol-8-amines establishes that a pyrrolo ring and a phenolic hydroxyl group can interact similarly with the dopamine receptor and provides evidence for the existence of a hydrogen-bond acceptor nucleus on the dopamine receptor macromolecule that is involved in the behavioral manifestations of dopamine agonists.
• Phenolic derivatives of 1,2-methano-N,N-dipropyl-1,2,3,4-tetrahydronaphth-2-ylamine. Structural hybrids of 2-aminotetralin- and phenylcyclopropylamine-derived 5-HT1A-receptor agonists
  作者：J Vallgårda、LE Arvidsson、BE Svensson、CJ Fowler、U Hacksell

  DOI：10.1016/0223-5234(93)90126-y

  日期：1993.1

  Three phenolic derivatives of 1,2-methano-N,N-dipropyl- 1,2,3,4-tetrahydronaphth-2-ylamine 6-8 were synthesized as structural hybrids of the potent 5-HT1A-receptor agonist 8-OH-DPAT 1 and 2 related phenolic phenylcyclopropylamines 4 and 5. The new compounds were assayed for 5-HT1A-receptor affinity and efficacy in vitro. Hybrids 6 and 7 were considered to be inactive but 8 had a K(i) value of 130 nM for [H-3]-8-OH-DPAT labelled 5-HT1A-receptors and produced an inhibition of the cAMP-production in the VIP-stimulated adenylyl cyclase assay. Thus, 8 is able to bind to and stimulate 5-HT1A-receptors. The results are discussed in relation to a previously described 3-D model for 5-HT1A-receptor agonists.