1,2,3,4,5,8-hexahydro-7-methoxy-N,N-dipropyl-2-naphthalenamine | 83343-26-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,2,3,4,5,8-hexahydro-7-methoxy-N,N-dipropyl-2-naphthalenamine
• 英文别名: 7-methoxy-N,N-dipropyl-1,2,3,4,5,8-hexahydronaphthalen-2-amine
• CAS: 83343-26-4
• 化学式: C₁₇H₂₉NO
• 分子量: 263.423
• InChiKey: MRDGYEIQTPDJBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  1,2,3,4,5,8-hexahydro-7-methoxy-N,N-dipropyl-2-naphthalenamine 在 吡啶 、 盐酸 、 盐酸羟胺 、 氢溴酸 、 溶剂黄146 、 sodium sulfate 作用下， 反应 3.0h， 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-OMe-DPAT 在 氨 作用下， 以 四氢呋喃 、 甲醇 、 水 、 异丙醇 、 丙酮 为溶剂， 生成 1,2,3,4,5,8-hexahydro-7-methoxy-N,N-dipropyl-2-naphthalenamine
  参考文献：
  名称：

  6,7,8,9-Tetrahydro-3H-benz[E]indol-8-amine derivatives

  摘要：

  这里披露了以下式的化合物##STR1##，其中R.sup.1，R.sup.2，R.sup.3，R.sup.4和R.sup.5分别是氢或较低的烷基，其治疗上可接受的酸盐，它们的制备方法，使用这些化合物的方法以及药物组合物。这些化合物在哺乳动物中表现出多巴胺受体刺激活性，并可用于治疗高催乳素血症、乳汁分泌、闭经、阳痿、帕金森病、糖尿病、肢端肥大症、高血压和其他中枢神经系统疾病。

  公开号：

  US04370341A1

文献信息

• 6,7,8,9-Tetrahydro-3H-benz[E]indol-8-amine derivatives
  申请人：Ayerst, McKenna & Harrison, Ltd.

  公开号：US04370341A1

  公开（公告）日：1983-01-25

  Herein is disclosed compounds of the formula ##STR1## in which R.sup.1,R.sup.2,R.sup.3,R.sup.4 and R.sup.5 each is hydrogen or lower alkyl, therapeutically acceptable acid addition salts thereof, processes for their preparation, methods of using the compounds and pharmaceutical compositions. The compounds exhibit dopamine-receptor stimulating activity in a mammal and are useful for treating hyperprolactinemia, galactorrhea, amenorrhea, impotence, Parkinsonism, diabetes, acromegaly, hypertension and other central nervous system disorders.

  这里披露了以下式的化合物##STR1##，其中R.sup.1，R.sup.2，R.sup.3，R.sup.4和R.sup.5分别是氢或较低的烷基，其治疗上可接受的酸盐，它们的制备方法，使用这些化合物的方法以及药物组合物。这些化合物在哺乳动物中表现出多巴胺受体刺激活性，并可用于治疗高催乳素血症、乳汁分泌、闭经、阳痿、帕金森病、糖尿病、肢端肥大症、高血压和其他中枢神经系统疾病。
• ASSELIN, A. A.;HUMBER, L. G.
  作者：ASSELIN, A. A.、HUMBER, L. G.

  DOI：——

  日期：——
• 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
• US4370341A
  申请人：——

  公开号：US4370341A

  公开（公告）日：1983-01-25
• 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.