(S)-7-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine | 161873-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (S)-7-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine
• 英文别名: (S)-(-)-7-methoxy-2-(n-propylamino)tetralin；(7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propylamine；((S)-7-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine；(2S)-7-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS: 161873-80-9
• 化学式: C₁₄H₂₁NO
• 分子量: 219.327
• InChiKey: RMRODALMKPMZFW-ZDUSSCGKSA-N

物化性质

• 沸点：
  338.3±42.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (7-甲氧基-1,2,3,4-四氢-萘-2-基)-丙基-胺 生成 (S)-7-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine
  参考文献：
  名称：

  Sonesson; Barf; Nilsson, Journal of Medicinal Chemistry, 1995, vol. 38, # 8, p. 1319 - 1329

  摘要：

  DOI：

文献信息

• Resolved monophenolic 2-aminotetralins and 1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolines: structural and stereochemical considerations for centrally acting pre- and postsynaptic dopamine-receptor agonists
  作者：Haakan Wikstroem、Bengt Andersson、Domingo Sanchez、Per Lindberg、Lars Erik Arvidsson、Anette M. Johansson、J. Lars G. Nilsson、Kjell Svensson、Stephan Hjorth、Arvid Carlsson

  DOI：10.1021/jm00380a012

  日期：1985.2

  centrally acting dopamine (DA) agonists acting on both pre- and postsynaptic DA receptors. The compounds resolved are 5- and 7-hydroxy-2-(di-n-propylamino)tetralin and cis- and trans-7-hydroxy-4-n-propyl-1,2,3,4,4a,5,6,10b-octahydrobenzo [f]quinoline. By the superimposition of the structures of the more active enantiomers of these compounds with those of known dopaminergic agonists, apomorphine and ergolines

  揭示了作用在突触前和突触后DA受体上的中枢作用多巴胺（DA）激动剂的详细结构-活性关系。解析出的化合物为5-和7-羟基-2-（二-正丙基氨基）四氢萘林和顺-和反7-羟基-4-正丙基-1,2,3,4,4a，5,6 ，10b-八氢苯并[f]喹啉。通过将这些化合物的更具活性的对映异构体的结构与已知的多巴胺能激动剂，阿扑吗啡和麦角灵重叠，可以提出一种新的DA受体模型，作为当前DA受体理论的产物。该受体模型最重要的概念之一是强调多巴胺能化合物的N取代基可能占据的位置。这些位置中的一个在空间上定义得很好，而另一个方向在空间上不太重要。该模型已被用来解释某些先前报道的结构缺乏多巴胺能活性，还用于预测新型结构的特性，包括固有手性，该结构应对DA受体具有活性。希望这种启发式DA受体模型将导致发现更多选择性和有效药理学工具，最终可能导致开发用于治疗中枢神经系统多巴胺能功能疾病的治疗剂。
• Discovery of 4-(4-(2-((5-Hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)(propyl)amino)ethyl)piperazin-1-yl)quinolin-8-ol and Its Analogues as Highly Potent Dopamine D2/D3 Agonists and as Iron Chelator: In Vivo Activity Indicates Potential Application in Symptomatic and Neuroprotective Therapy for Parkinson’s Disease
  作者：Balaram Ghosh、Tamara Antonio、Maarten E. A. Reith、Aloke K. Dutta

  DOI：10.1021/jm901618d

  日期：2010.3.11

  The role of iron in the pathogenesis of Parkinson's disease (PD) has been implicated strongly because of generation of oxidative stress leading to dopamine cell death. In our overall goal to develop bifunctional/multifunctional drugs, we designed dopamine D2/D3 agonist molecules with a capacity to bind to iron. Binding assays were carried out with HEK-293 cells expressing either D2 or D3 receptor with tritiated spiperone to evaluate inhibition constants (K-i). Functional activity of selected compounds was carried out with GTP gamma S binding assay. SAR results identified compounds (+)-19a and (-)-19b as two Potent agonists for both D2 and D3 receptors (EC50 (GTP gamma S); D2 = 4.51 and 1.69 nM and D3 = 1.58 and 0.74 nM for (-)-19b and (+)-19a, respectively). In vitro complexation Studies with 19b demonstrated efficient chelation with iron. Furthermore, the deoxyribose assay with 19b demonstrated potent antioxidant activity. In PD animal model study, (-)-19b exhibited potent in vivo activity in reversing locomotor activity in reserpinized rats and also in producing potent rotational activity in 6-OHDA lesioned rats. This reports initial development of unique lead molecules that might find potential use in Symptomatic and neuroprotective treatment of PD.
• US6008219A
  申请人：——

  公开号：US6008219A

  公开（公告）日：1999-12-28
• [EN] NEW CENTRALLY ACTING 5-, 6-, 7-, AND 8-SUBSTITUTED SULPHONE ESTERS OF N-MONOSUBSTITUTED 2-AMINOTETRALINS AND RELATED STRUCTURES<br/>[FR] NOUVEAUX ESTERS DE SULPHONE A SUBSTITUTION EN 5,6,7 ET 8 DE 2-AMINOTETRALINES N-MONOSUBSTITUEES A ACTION CENTRALE ET STRUCTURES APPARENTEES
  申请人：DAMSMA-BLOEM, Anette, J.

  公开号：WO1994026703A1

  公开（公告）日：1994-11-24

  (EN) A compound of formula (1) or pharmaceutically acceptable acid addition salts thereof, wherein R1 is H, (C1-C8) alkyl, alkenyl, alkynyl, cyclopropylalkyl or (C1-C8) haloalkyl; X is CH2, O or S; R2-SO2-O is in position 5, 6, 7 or 8 and R2 is CF3, CF2CF3, C1-C8 alkyl, substituted aryl (e.g. 4-toluyl); R3 is H, CH3 or CH2CH3. When R3 is CH3 or CH2CH3, it is always in a cis-relationship with respect to the 2-amine substituent.(FR) Composé de formule (1) ou sels d'addition d'acide de ce composé acceptables en pharmacologie. Dans la formule, R1 représente H, alkyle en C1-C8, alcényle, alkynyle, cyclopropylalkyle ou haloalkyle en C1-C8; X représente CH2, O ou S; R2-SO2-O est en position 5,6,7 ou 8 et R2 représente CF3, CF2CF3, alkyle en C1-C8, aryle substitué (par exemple 4-toluyle); R3 représente H, CH3 ou CH2CH3. Lorsque R3 représente CH3 ou CH2CH3, il est toujours en relation cis par rapport au substituant 2-amine.
• Sonesson; Barf; Nilsson, Journal of Medicinal Chemistry, 1995, vol. 38, # 8, p. 1319 - 1329
  作者：Sonesson、Barf、Nilsson、Dijkstra、Carlsson、Svensson、Smith、Martin、Duncan、King、Wikstrom

  DOI：——

  日期：——