1,2,3,4-tetrahydro-5,6-dimethoxy-N-propyl-2-naphthaleneamine | 58352-88-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2,3,4-tetrahydro-5,6-dimethoxy-N-propyl-2-naphthaleneamine
• 英文别名: 5,6-Dimethoxy-2-n-propylamino-1,2,3,4-tetrahydronaphthalin；5,6-dimethoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS: 58352-88-8
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: RUPKFZHUNWFYQT-UHFFFAOYSA-N

物化性质

• 沸点：
  374.7±42.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-5,6-dimethoxy-N-propyl-2-naphthaleneamine 在 氢碘酸 、 乙酸酐 作用下， 生成 5,6-Dihydroxy-2-n-propylamino-1,2,3,4-tetrahydronaphthalin
  参考文献：
  名称：

  Synthesis and pharmacology of some 2-aminotetralins. Dopamine receptor agonists

  摘要：

  A series of 2-amino-1,2,3,4-tetrahydronaphthalene compounds bearing substituents on the nitrogen and in the aromatic ring was synthesized from beta-tetralone intermediates. Compounds were screened in vivo for dopaminergic activity using tests in which apomorphine was especially active. It was found that apparent dopaminergic activity is inherent in 2-dialkylaminotetralins, the dipropylamine substitution being the most consistently productive amine group studies. Activity was greatly enhanced by proper substitution in the aromatic ring. The 5,6-dihydroxy group was the best potentiating group found. These data support the idea that the extended conformation for the phenylethylamine moiety of ampmorphine and dopamine is favorable for dopaminergic agonist activity. They also suggest that an unetherified catechol group may not be essential for such activity.

  DOI：

  10.1021/jm00238a008
• 作为产物：
  描述：

  1,2,6-三甲氧基萘 在 乙醇 、 sodium 作用下， 生成 1,2,3,4-tetrahydro-5,6-dimethoxy-N-propyl-2-naphthaleneamine
  参考文献：
  名称：

  Synthesis and pharmacology of some 2-aminotetralins. Dopamine receptor agonists

  摘要：

  A series of 2-amino-1,2,3,4-tetrahydronaphthalene compounds bearing substituents on the nitrogen and in the aromatic ring was synthesized from beta-tetralone intermediates. Compounds were screened in vivo for dopaminergic activity using tests in which apomorphine was especially active. It was found that apparent dopaminergic activity is inherent in 2-dialkylaminotetralins, the dipropylamine substitution being the most consistently productive amine group studies. Activity was greatly enhanced by proper substitution in the aromatic ring. The 5,6-dihydroxy group was the best potentiating group found. These data support the idea that the extended conformation for the phenylethylamine moiety of ampmorphine and dopamine is favorable for dopaminergic agonist activity. They also suggest that an unetherified catechol group may not be essential for such activity.

  DOI：

  10.1021/jm00238a008

文献信息

• Synthesis and pharmacological evaluation of 5,6,7,8-tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1,2-naphthalenediol: A novel non-selective dopamine-receptor agonist
  作者：Swier Copinga、Durk Dijkstra、Jan B. de Vries、Cor J. Grol、Alan S. Horn

  DOI：10.1002/recl.19931120211

  日期：——

  of dopamine D1 and -D2 receptors could be beneficial for the treatment of Parkinson's disease7,13, we prepared 5,6,7,8-tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1,2-naphthalenediol (PTAT. 4), the diol analogue of N-0437 (3), as a potential mixed D1/D2-receptor agonist. The synthesis of 4 was carried out via a new strategy. The crucial step in this strategy was the conversion of 1-diazo-4-(2,3

  基于多巴胺D 1和-D 2受体同时刺激可能有益于帕金森氏病7,13的假设，我们制备了5,6,7,8-tetrahydro-6- [propyl [2-（2噻吩基）乙基]氨基] -1,2-萘二酚（PTAT。4）中，N-0437（二醇类似物3），作为一个潜在的混合d 1 / d 2受体激动剂。4的合成是通过新策略进行的。该策略的关键步骤是将1-重氮-4-（2,3-二甲氧基苯基）-2-丁酮（15）转化为关键的中间体5,6-二甲氧基-2-四氢萘酮（9通过乙酸铑（II）催化的环化反应，然后在三氟乙酸的影响下进行转化。对PTAT（4）的多巴胺能性质的药理评估表明，该化合物对D 1和D 2受体均显示出高亲和力，并且具有与DAT（D 1 / D 2受体混合激动剂）DPAT（1）相同的诱导能力。利血平使小鼠的运动活动呈现急性运动性。
• HACKSELL U.; SVENSSON U.; NILSSON J. L. G.; HJORTH S.; CARLSSON A.; WIKST+, J. MED. CHEM., 1979, 22, NO 12, 1469-1475
  作者：HACKSELL U.、 SVENSSON U.、 NILSSON J. L. G.、 HJORTH S.、 CARLSSON A.、 WIKST+

  DOI：——

  日期：——
• DERIVATIVES OF 2-AMINO-1,2,3,4-TETRAHYDRONAPHTHALENE ACTIVE ON THE CARDIOVASCULAR SYSTEM
  申请人：ZAMBON GROUP S.p.A.

  公开号：EP0719252A1

  公开（公告）日：1996-07-03
• Synthesis and pharmacology of some 2-aminotetralins. Dopamine receptor agonists
  作者：John D. McDermed、Gerald M. McKenzie、Arthur P. Phillips

  DOI：10.1021/jm00238a008

  日期：1975.4

  A series of 2-amino-1,2,3,4-tetrahydronaphthalene compounds bearing substituents on the nitrogen and in the aromatic ring was synthesized from beta-tetralone intermediates. Compounds were screened in vivo for dopaminergic activity using tests in which apomorphine was especially active. It was found that apparent dopaminergic activity is inherent in 2-dialkylaminotetralins, the dipropylamine substitution being the most consistently productive amine group studies. Activity was greatly enhanced by proper substitution in the aromatic ring. The 5,6-dihydroxy group was the best potentiating group found. These data support the idea that the extended conformation for the phenylethylamine moiety of ampmorphine and dopamine is favorable for dopaminergic agonist activity. They also suggest that an unetherified catechol group may not be essential for such activity.