7-(dimethylamino)-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one | 83343-30-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-(dimethylamino)-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one
• CAS: 83343-30-0
• 化学式: C₁₂H₁₉NO
• 分子量: 193.289
• InChiKey: ZKYVWGYBDJKIFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N-dimethyl-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine 在 盐酸 、 氨 、 sodium 、 异丙醇 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 1.25h， 生成 7-(dimethylamino)-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one
  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

文献信息

• 6,7,8,9-Tetrahydro-3H-benz(e)indolamine derivatives, processes for their preparation and intermediates used therein, and pharmaceutical compositions containing the indolamine derivatives
  申请人：AYERST, MCKENNA AND HARRISON INC.

  公开号：EP0055043B1

  公开（公告）日：1985-01-23
• 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.