(+/-)-5,6-dimethoxy-2-(N,N-di-n-propylamino)tetralin | 94844-53-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (+/-)-5,6-dimethoxy-2-(N,N-di-n-propylamino)tetralin
• 英文别名: 5,6-Dimethoxy-2-di-n-propylamino-1,2,3,4-tetrahydronaphthalin；5,6-dimethoxy-N,N-dipropyl-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS: 94844-53-8
• 化学式: C₁₈H₂₉NO₂
• 分子量: 291.434
• InChiKey: IIUCMKGUBKBZJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-5,6-dimethoxy-2-(N,N-di-n-propylamino)tetralin 在 氢碘酸 、 乙酸酐 作用下， 生成 2-(二-n-丙氨基)-5,6-二羟基四氢萘
  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 (+/-)-5,6-dimethoxy-2-(N,N-di-n-propylamino)tetralin
  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

• Resolution of 5,6-Dihydroxy-2-(N,N-di -n-propylamino)tetralin in Relation to the Structural and Stereochemical Requirements for Centrally Acting Dopamine Agonists
  作者：Cor J. Grol、Liesbeth J. Jansen、Hans Rollema

  DOI：10.1021/jm50001a024

  日期：1985.5

  The enantiomers of 5,6-dimethoxy-2-(N,N-dipropylamino)tetralin were prepared with use of (+)- and (-)-dibenzoyltartaric acid as the resolving agent. Ether cleavage with BBr3 gave the enantiomers of the dihydroxy compound 5,6-dihydroxy-2-(N,N-dipropylamino)tetralin (5,6-(OH)2-DPATN). The in vitro activities of (+)- and (-)-5,6-(OH)2-DPATN were evaluated in binding studies with rat striatal tissue with use of [3H]-N-n-propylnorapomorphine (NPA) as the ligand. IC50 (nM) values for (-)- and (+)-5,6-(OH)2-DPATN were 2.5 and 400, respectively. The in vivo efficacy of the enantiomers was evaluated by examining their effects on the metabolism of dopamine in rat striatum. After a 0.5 mumol/kg ip injection of the (-) enantiomer, the concentrations of the metabolites HVA and DOPAC were reduced to 50% of control values, whereas at this dose the (+) isomer was inactive. On the basis of these findings together with the stereochemical data of previously described DA agonists, a dopamine-receptor model has been developed which consists of two binding sites for the amine nitrogen of DA agonists in addition to a major binding sit for the m-hydroxy group. The relevance of this model with its accessory features is discussed in relation to the structure and pharmacological data of different DA agonists.
• 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.